138 results on '"Zbigniew Karczmarzyk"'
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2. Potential Anticancer Agents against Melanoma Cells Based on an As-Synthesized Thiosemicarbazide Derivative
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Paweł Kozyra, Agnieszka Korga-Plewko, Zbigniew Karczmarzyk, Anna Hawrył, Waldemar Wysocki, Michał Człapski, Magdalena Iwan, Marta Ostrowska-Leśko, Emilia Fornal, and Monika Pitucha
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synthesis ,thiosemicarbazide ,X-ray investigation ,melanoma ,anticancer activity ,Microbiology ,QR1-502 - Abstract
In this paper, thiosemicarbazide derivatives were synthesized as potential anticancer agents. X-ray investigations for 1-(2,4-dichlorophenoxy)acetyl-4-(2-fluorophenyl) thiosemicarbazide, 1-(2,4-dichlorophenoxy)acetyl-4-(4-metylothiophenyl)thiosemicarbazide and 1-(2,4-di chlorophenoxy)acetyl-4-(4-iodophenyl)thiosemicarbazide were carried out in order to confirm the synthesis pathways, identify their tautomeric forms, analyze the conformational preferences of molecules, and identify intra- and intermolecular interactions in the crystalline state. TLC and RP-HPLC analyses were used to determine lipophilicity. The lipophilicity analysis revealed that the 4-substituted halogen derivatives of thiosemicarbazides showed greater lipophilicity compared with 2-substituted derivatives. The optimal range of lipophilicity for biologically active compounds logkw is between 4.14 and 4.78. However, as the analysis showed, it is not a decisive parameter. The cytotoxicity of the new compounds was evaluated against both the G-361 and BJ cell lines. Cytotoxicity analyses and cell-cycle and cell apoptosis assays were performed. The MTT test demonstrated that three compounds were cytotoxic to melanoma cells and not toxic to normal fibroblasts in the concentration range used. The cell cycle analysis showed that the compounds had no significant effect on the cell cycle inhibition. An extensive gene expression analysis additionally revealed that all compounds tested downregulated the expression of dihydroorotate dehydrogenase (DHODH). DHODH is a mitochondrial enzyme involved in the de novo synthesis of pyrimidines. Due to the rapid rate of cancer cell proliferation and the increased demand for nucleotide synthesis, it has become a potential therapeutic target.
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- 2022
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3. Chiral Pyrazolo[4,3-e][1,2,4]triazine Sulfonamides—Their Biological Activity, Lipophilicity, Protein Affinity, and Metabolic Transformations
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Zofia Bernat, Anna Mieszkowska, Zofia Mazerska, Joanna Matysiak, Zbigniew Karczmarzyk, Katarzyna Kotwica-Mojzych, and Mariusz Mojzych
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pyrazolo[4,3-e][1,2,4]triazine sulfonamides ,tyrosinase inhibitors ,urease inhibitors ,molecular docking ,affinity chromatography ,Technology ,Engineering (General). Civil engineering (General) ,TA1-2040 ,Biology (General) ,QH301-705.5 ,Physics ,QC1-999 ,Chemistry ,QD1-999 - Abstract
Referring to our previous laboratory results related to the tyrosinase and urease inhibition by pyrazolo[4,3-e][1,2,4]triazine sulfonamides, we examined here in silico the mechanism of action at the molecular level of the investigated pyrazolotriazine sulfonamides by the molecular docking method. The studied compounds being evaluated for their cytotoxic effect against cancer cell lines (MCF-7, K-562) and for recombinant Abl and CDK2/E kinase inhibitory potency turned out to be inactive in these tests. The pyrazolotriazines were also investigated with respect to their lipophilicity and plasma protein binding using HPLC chromatography in isocratic conditions. The observed small affinity for plasma proteins could be advantageous in the potential in vivo studies. Moreover, the compounds were sensitive to metabolic transformations with phase I enzymes, which led to the hydroxylation and dealkylation products, whereas phase II transformations did not occur.
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- 2021
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4. Influence of Complexation of Thiosemicarbazone Derivatives with Cu (II) Ions on Their Antitumor Activity against Melanoma Cells
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Monika Pitucha, Agnieszka Korga-Plewko, Agnieszka Czylkowska, Bartłomiej Rogalewicz, Monika Drozd, Magdalena Iwan, Joanna Kubik, Ewelina Humeniuk, Grzegorz Adamczuk, Zbigniew Karczmarzyk, Emilia Fornal, Waldemar Wysocki, and Paulina Bartnik
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synthesis ,thiosemicarbazone ,X-ray investigation ,copper(II) complex ,TG-DTG techniques ,melanoma ,Biology (General) ,QH301-705.5 ,Chemistry ,QD1-999 - Abstract
A series of thiosemicarbazone derivatives was prepared and their anti-tumor activity in vitro was tested. The X-ray investigation performed for compounds T2, T3 and T5 confirmed the synthesis pathway and assumed molecular structures of analyzed thiosemicarbazones. The conformational preferences of the thiosemicarbazone system were characterized using theoretical calculations by AM1 method. Selected compounds were converted into complexes of Cu (II) ions. The effect of complexing on anti-tumor activity has been investigated. The copper(II) complexes, with Schiff bases T1, T10, T12, T13, and T16 have been synthesized and characterized by chemical and elemental analysis, FTIR spectroscopy and TGA method. Thermal properties of coordination compounds were studied using TG-DTG techniques under dry air atmosphere. G361, A375, and SK-MEL-28 human melanoma cells and BJ human normal fibroblast cells were treated with tested compounds and their cytotoxicity was evaluated with MTT test. The compounds with the most promising anti-tumour activity were then selected and their cytotoxicity was verified with cell cycle analysis and apoptosis/necrosis detection. Additionally, DNA damages in the form of a basic sites presence and the expression of oxidative stress and DNA damage response genes were evaluated. The obtained results indicate that complexation of thiosemicarbazone derivatives with Cu (II) ions improves their antitumor activity against melanoma cells. The observed cytotoxic effect is associated with DNA damage and G2/M phase of cell cycle arrest as well as disorders of the antioxidant enzymes expression.
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- 2021
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5. New Application of 1,2,4-Triazole Derivatives as Antitubercular Agents. Structure, In Vitro Screening and Docking Studies
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Zbigniew Karczmarzyk, Marta Swatko-Ossor, Waldemar Wysocki, Monika Drozd, Grazyna Ginalska, Anna Pachuta-Stec, and Monika Pitucha
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1,2,4-triazole ,structure ,X-ray analysis ,antitubercular agent ,molecular docking ,Organic chemistry ,QD241-441 - Abstract
A series of 1,2,4-triazole derivatives were synthesized and assigned as potential anti-tuberculosis substances. The molecular and crystal structures for the model compounds C1, C12, and C13 were determined using X-ray analysis. The X-ray investigation confirmed the synthesis pathway and the assumed molecular structures for analyzed 1,2,4-triazol-5-thione derivatives. The conformational preferences resulting from rotational degrees of freedom of the 1,2,4-triazole ring substituents were characterized. The lipophilicity (logP) and electronic parameters as the energy of frontier orbitals, dipole moments, NBO net charge distribution on the atoms, and electrostatic potential distribution for all structures were calculated at AM1 and DFT/B3LYP/6-311++G(d,p) level. The in vitro test was done against M. tuberculosis H37Ra, M. phlei, M. smegmatis, and M. timereck. The obtained results clearly confirmed the antituberculosis potential of compound C4, which turned out to be the most active against Mycobacterium H37Ra (MIC = 0.976 μg/mL), Mycobaterium pheli (MIC = 7.81 μg/mL) and Mycobacerium timereck (62.6 μg/mL). Satisfactory results were obtained with compounds C8, C11, C14 versus Myc. H37Ra, Myc. pheli, Myc. timereck (MIC = 31.25−62.5 μg/mL). The molecular docking studies were carried out for all investigated compounds using the Mycobacterium tuberculosis cytochrome P450 CYP121 enzyme as molecular a target connected with antimycobacterial activity.
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- 2020
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6. 1,2,4-Triazine Sulfonamides: Synthesis by Sulfenamide Intermediates, In Vitro Anticancer Screening, Structural Characterization, and Molecular Docking Study
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Danuta Branowska, Zbigniew Karczmarzyk, Ewa Wolińska, Waldemar Wysocki, Maja Morawiak, Zofia Urbańczyk-Lipkowska, Anna Bielawska, and Krzysztof Bielawski
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anticancer activity ,conformational analysis ,molecular docking ,sulfonamides ,X-ray analysis ,Organic chemistry ,QD241-441 - Abstract
In this study, we synthesized novel sulfonamides with a 1,2,4-triazine moiety according to pharmacophore requirements for biological activity. All the synthesized compounds were tested in vitro to verify whether they exhibited anticancer activity against the human breast cancer cell lines MCF-7 and MDA-MB-231. Among them, two most active ones, having IC50 values of 50 and 42 µM, respectively, were found to show higher anticancer activity than chlorambucil used as the reference in the in vitro tests. In addition, two other compounds, which had IC50 values of 78 and 91 µM, respectively, exhibited a similar level of activity as chlorambucil. X-ray analysis carried out for two of the compounds confirmed their synthesis pathway as well as their assumed molecular structures. Furthermore, a conformational analysis was performed, and electronic parameters of molecules were characterized using theoretical calculations at AM1 and DFT level. Moreover, molecular docking revealed the mode of binding of the investigated 1,2,4-triazine sulfonamides with the human estrogen receptor alpha (ERα).
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- 2020
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7. Synthesis, Structural Characterization, and Biological Activity of New Pyrazolo[4,3-e][1,2,4]triazine Acyclonucleosides
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Mariusz Mojzych, Zofia Bernat, Zbigniew Karczmarzyk, Joanna Matysiak, and Andrzej Fruziński
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acyclonucleosides ,pyrazolo[4,3-e][1,2,4]triazine ,anticancer activity ,x-ray analysis ,theoretical calculation ,molecular docking ,Organic chemistry ,QD241-441 - Abstract
A series of new pyrazolo[4,3-e][1,2,4]triazine acyclonucleosides 2−5 and 8 were prepared and evaluated for their anticancer activity against human cancer cell lines (MCF-7, K-562) and CDK2/E, as well as Abl protein kinases inhibitors. Lipophilicity of the compounds was determined using C-18 and immobilized artificial membrane (IAM) chromatography. In order to confirm the molecular structures and synthesis pathway of new acyclonucleosides, X-ray analysis was performed for model compound 3. Theoretical calculations at the DFT/B3LYP/6-311++G(d,p) level were used for the characterization of electronic structures of 1−8. The potential antiviral activity of acyclonucleosides 2−8 was tested in silico using molecular docking method.
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- 2020
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8. Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity
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Tomasz M. Wróbel, Urszula Kosikowska, Agnieszka A. Kaczor, Sylwia Andrzejczuk, Zbigniew Karczmarzyk, Waldemar Wysocki, Zofia Urbańczyk-Lipkowska, Maja Morawiak, and Dariusz Matosiuk
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antifungal ,Candida albicans ,X-ray analysis ,14-α-sterol demethylase ,molecular modelling ,synthesis ,Organic chemistry ,QD241-441 - Abstract
Six novel imidazoline derivatives were synthesized and tested in antifungal assays. One of the compounds, N-cyclohexyl-2-imino-3-(4-nitrophenyl)imidazolidine-1-carboxamide showed moderate activity against several clinical strains of Candida albicans. Its structure was solved by X-ray crystallography and its mode of action was deduced using molecular modelling. It was found to be similar to that of fluconazole. The potential for further optimization including SAR of the compound is briefly discussed.
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- 2015
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9. Synthesis, In Vitro Screening and Docking Studies of New Thiosemicarbazide Derivatives as Antitubercular Agents
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Monika Pitucha, Zbigniew Karczmarzyk, Marta Swatko-Ossor, Waldemar Wysocki, Maciej Wos, Kamil Chudzik, Grazyna Ginalska, and Andrzej Fruzinski
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synthesis ,thiosemicarbazide ,X-ray analysis ,tuberculosis ,molecular docking ,Organic chemistry ,QD241-441 - Abstract
A series of thiosemicarbazide derivatives was designed and synthesized by reaction of carboxylic acid hydrazide with isothiocyanates. The molecular structures of the investigated thiosemicarbazides were confirmed and characterized by spectroscopic analysis. The conformational preference of carbonylthiosemicarbazide chain and intra- and intermolecular interactions in the crystalline state were characterized using X-ray analysis. The antituberculosis activity of the target compounds were tested in vitro against four Mycobacterium strains: M. H37Ra, M. phlei, M. smegmatis, M. timereck. The most active compounds were those with 2-pyridine ring. They exhibited lower minimal inhibitory concentration (MIC) values in the range 7.81–31.25 μg/mL in comparison to the other isomers. Compound 5 had activity against M. smegmatis at a concentration of 7.81 μg/mL whereas compound 2 had activity against all tested strains at a concentration of 15.625 μg/mL. The molecular docking studies were performed for investigated compounds using the Mycobacterium tuberculosis glutamine synthetase MtGS as their molecular target.
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- 2019
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10. A facile approach to 2,2′-bipyridine based thiacrown ethers and their sulfoxides by DA-rDA reaction of 5,5′-bi-1,2,4-triazine thiamacrocycles. The conformation studies
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Justyna Ławecka, Zbigniew Karczmarzyk, Ewa Olender, Ewa Wolińska, Danuta Branowska, and Andrzej Rykowski
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Organic chemistry ,QD241-441 - Published
- 2011
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11. 3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione
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Zbigniew Karczmarzyk, Monika Pitucha, Waldemar Wysocki, Anna Pachuta-Stec, and Andrzej Stańczuk
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Crystallography ,QD901-999 - Abstract
The title compound, C11H13N3S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C—H...S contact. In the crystal, pairs of N—H...S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively.
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- 2013
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12. 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)aniline
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Mariusz Mojzych, Zbigniew Karczmarzyk, and Andrzej Fruziński
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Crystallography ,QD901-999 - Abstract
The title compound, C21H16N4, obtained under standard Suzuki cross-coupling conditions, is a model compound in the synthesis and biological activity evaluation of new aza-analogues of sildenafil containing a pyrazolo[4,3-e][1,2,4]triazine system. An N—H...N intramolecular hydrogen bond involving the aminobenzene system and the 1,2,4-triazine moiety helps to establish a near coplanar orientation of the rings with a dihedral angle of 12.04 (4)°, which is believed to be necessary for the biological activity of sildenafil analogues. The 1,2,4-triazine ring is slightly distorted from planarity [r.m.s deviation = 0.0299 (11) Å] and forms dihedral angles of 58.60 (4) and 36.35 (3)° with the pendant phenyl rings. The crystal packing features bifurcated N—H...(N,N) hydrogen bonds linking screw-axis-related molecules into chains parallel to the [010] direction< and π–π interactions, with a centroid–centroid separation of 3.8722 (7) Å and a slippage of 1.412 (3) Å. The crystal studied was a nonmerohedral twin with a ratio of 0.707 (2):0293 (2).
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- 2012
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13. Ethyl 2-(3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetate
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Zbigniew Karczmarzyk, Monika Pitucha, Waldemar Wysocki, Andrzej Fruziński, and Ewa Olender
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Crystallography ,QD901-999 - Abstract
The title compound, C7H11N3O2S, exists in the 5-thioxo tautomeric form. The 1,2,4-triazoline ring is essentially planar, with a maximum deviation of 0.010 (2) Å for the substituted N atom. The ethyl acetate substituent is almost planar, with a maximum deviation of 0.061 (4) Å for the methylene C atom of the ethoxy group. The angle between the mean plane of this substituent and the mean plane of the 1,2,4-triazoline ring is 89.74 (8)°. In the crystal, molecules are linked by a combination of N—H...S, C—H...N and C—H...O hydrogen bonds into chains parallel to [100].
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- 2012
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14. 2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile
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Ewa Wolińska, Zbigniew Karczmarzyk, Andrzej Rykowski, Zofia Urbańczyk-Lipkowska, and Przemysław Kalicki
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Crystallography ,QD901-999 - Abstract
The title compound, C19H17ClN4, was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intramolecular C—H...N interactions occur. In the crystal, molecules related by a c-glide plane are linked into zigzag chains along [001] by N—H...N hydrogen bonds.
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- 2012
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15. 5,5′,6,6′-Tetramethyl-3,3′-bi-1,2,4-triazine
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Ewa Wolińska, Zbigniew Karczmarzyk, Andrzej Rykowski, and Waldemar Wysocki
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Crystallography ,QD901-999 - Abstract
In the title compound, C10H12N6, the two 5,6-dimethyl-1,2,4-triazine halves of the molecule are related by a centre of symmetry. The two triazine rings are coplanar to within a maximum deviation of 0.013 (2) Å from the mean plane of the ring atoms. In the crystal, molecules form layers parallel to the (100) crystallographic plane. Adjacent layers are held together via a C—H...π interaction involving molecules related by an a-glide plane.
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- 2011
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16. 5,6,7,8-Tetrahydroquinolin-8-one
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Teodozja M. Lipińska, Zbigniew Karczmarzyk, Waldemar Wysocki, Ewa Gruba, and Andrzej Fruziński
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Crystallography ,QD901-999 - Abstract
In the quinoline fused-ring system of the title compound, C9H9NO, the pyridine ring is planar to within 0.011 (3) Å, while the partially saturated cyclohexene ring adopts a sofa conformation with an asymmetry parameter ΔCs(C6) = 1.5 (4)°. There are no classical hydrogen bonds in the crystal structure. Molecules form molecular layers parallel to (100) with a distance between the layers of a/2 = 3.468 Å.
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- 2011
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17. 1,3-Dimethyl-5-methylsulfonyl-1H-pyrazolo[4,3-e][1,2,4]triazine
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Waldemar Wysocki, Zbigniew Karczmarzyk, and Mariusz Mojzych
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Crystallography ,QD901-999 - Abstract
In the title compound, C7H9N5O2S, the pyrazolo[4,3-e][1,2,4]triazine fused-ring system is essentially planar [maximum deviation = 0.0420 (3) Å]. In the crystal, molecules related by twofold axes are linked into a molecular net via intermolecular C—H...O and C—H...N hydrogen bonds. π–π interactions are observed between the triazine and pyrazole rings of molecules related by the the twofold axis and inversion symmetry with centroid–centroid distances of 3.778 (3) and 3.416 (3) Å, respectively.
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- 2010
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18. 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
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Waldemar Wysocki, Dariusz Matosiuk, Marzena Rządkowska, Zbigniew Karczmarzyk, Zofia Urbańczyk-Lipkowska, and Przemysław Kalicki
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Crystallography ,QD901-999 - Abstract
The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H...O and C—H...N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H...O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H...Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å].
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- 2010
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19. 5,6,7,8-Tetrahydroquinoline 1-oxide hemihydrate
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Zbigniew Karczmarzyk, Teodozja M. Lipińska, Waldemar Wysocki, Zofia Urbańczyk-Lipkowska, and Przemysław Kalicki
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Crystallography ,QD901-999 - Abstract
In the title compound, C9H11NO·0.5H2O, the asymmetric unit contains two similar molecules of 5,6,7,8-tetrahydroquinoline 1-oxide and one water molecule. The water molecule links the two O atoms of both independent N-oxides into dimers via O—H...O hydrogen bonds, forming a three-dimensional network along [101], which is additionally stabilized by weak C—H...O intermolecular interactions. In each molecule, the saturated six-membered rings exist in a conformation intermediate between a half-chair and sofa.
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- 2010
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20. 1,2-Bis[1-(3-methylsulfanyl-1,2,4-triazin-5-yl)ethylidene]diazane
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Mariusz Mojzych, Zbigniew Karczmarzyk, Zofia Urbańczyk-Lipkowska, and Przemysław Kalicki
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Crystallography ,QD901-999 - Abstract
The molecule of the title compound, C12H14N8S2, has an N—N gauche conformation. The triazine rings are nearly coplanar with respect to the imide bonds [C—C—C—N torsion angles = −15.3 (3) and −15.8 (3)°] and they are twisted by 77.88 (7)°. The overall conformation of the molecule is stabilized by intramolecular C—H...N hydrogen bonding. The molecular packing is influenced by π–π interactions of the triazine systems with a shortest centroid–centroid separation of 3.5242 (12) Å.
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- 2009
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21. 1-(3-Chlorophenyl)-3-(1-p-tolylimidazolidin-2-ylidene)urea
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Waldemar Wysocki, Dariusz Matosiuk, Zbigniew Karczmarzyk, Sylwia Fidecka, and Andrzej Fruziński
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Crystallography ,QD901-999 - Abstract
In the crystal structure of the title compound, C17H17ClN4O, the existence of only one 2-imino–oxo of the five possible N-amino–imino/O-keto–hydroxy tautomers is observed and the dihedral angle between the aromatic rings is 29.78 (11)°. The molecular conformation is stabilized by intramolecular C—H...N, N—H...O and C—H...O hydrogen bonds, in each case generating a six-membered ring. In the crystal structure, the glide-plane-related molecules are linked into C(4) amide chains by intermolecular N—H...O hydrogen bonds, and an intermolecular C—H...O link also occurs.
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- 2009
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22. (E)-1-(Pyridin-2-yl)ethanone O-acryloyloxime
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Andrzej Fruziński, Zbigniew Karczmarzyk, and Mariusz Mojzych
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Crystallography ,QD901-999 - Abstract
The title compound, C10H10N2O2, was synthesized by the reaction of the oxime of 2-acetylpyridine and 3-bromopropanoyl chloride in the presence of triethylamine. The molecule adopts a nearly planar chain-extended conformation with the oxime group in a trans and the acryloyl group in an s-cis conformation. This conformation is stabilized by an intramolecular C—H...N hydrogen bond. The screw-related molecules are linked into C(9) chains by C—H...O hydrogen bonds.
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- 2008
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23. Synthesis, structure and sulfonamide–sulfonimide tautomerism of sulfonamide–1,2,4-triazine derivatives
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Danuta Branowska, Waldemar Wysocki, Ewa Wolińska, Karolina Koc, Katarzyna Stańska, Barbara Mirosław, and Zbigniew Karczmarzyk
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Models, Molecular ,Inorganic Chemistry ,Sulfonamides ,Triazines ,Materials Chemistry ,Hydrogen Bonding ,Physical and Theoretical Chemistry ,Crystallography, X-Ray ,Condensed Matter Physics - Abstract
Two new 1,2,4-triazine-containing sulfonamide derivatives, namely, 4-bromo-N-(5,6-diphenyl-2H-1,2,4-triazin-3-ylidene)benzenesulfonamide, C21H15BrN4O4S, 3a, and methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamoyl]methyl}benzoate, C24H20N4O4S, 3b, which crystallize in the different sulfonimide and sulfonamide tautomeric forms, respectively, were synthesized and characterized by spectroscopic, X-ray diffraction and theoretical calculation methods. Both molecules adopt a very similar conformation of the common part of the structure and the differences occur within the substituents on the sulfonamide group. The amino groups characteristic for the existing tautomeric forms are involved in strong intermolecular N—H...N and N—H...O hydrogen bonds in 3a and 3b, respectively. The Hirshfeld surface analysis showed that H...H contacts constitute a high percentage of the intermolecular interactions. Theoretical calculations at the ab initio DFT/B3LYP/6-311++G(d,p) level showed that the two tautomeric forms observed for 3a and 3b can co-exist in chloroform, ethanol and water solutions, with a distinct predominance of the sulfonamide form; the participation of the sulfonimide form increases with increasing solvent polarity.
- Published
- 2022
24. Experimental and computational studies of tautomerism pyridine carbonyl thiosemicarbazide derivatives
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Paweł Kozyra, Agnieszka Kaczor, Zbigniew Karczmarzyk, Waldemar Wysocki, and Monika Pitucha
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Physical and Theoretical Chemistry ,Condensed Matter Physics - Abstract
Tautomerism is one of the most important phenomena to consider when designing biologically active molecules. In this work, we use NMR spectroscopy, IR, and X-ray analysis as well as quantum-chemical calculations in the gas phase and in a solvent to study tautomerism of 1- (2-, 3- and 4-pyridinecarbonyl)-4-substituted thiosemicarbazide derivatives. The tautomer containing both carbonyl and thione groups turned out to be the most stable. The results of the calculations are consistent with the experimental data obtained from NMR and IR spectroscopy and with the crystalline forms from the X-ray studies. The obtained results broaden the knowledge in the field of structural studies of the thiosemicarbazide scaffold, which will translate into an understanding of the interactions of compounds with a potential molecular target.
- Published
- 2023
25. Synthesis and structures of three new pyridine-containing oxazoline ligands of complexes for asymmetric catalysis
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Ewa Wolińska, Waldemar Wysocki, Zbigniew Karczmarzyk, and Danuta Branowska
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Ligand ,Hydrogen bond ,Enantioselective synthesis ,Crystal structure ,Oxazoline ,Condensed Matter Physics ,Ring (chemistry) ,Inorganic Chemistry ,chemistry.chemical_compound ,Crystallography ,chemistry ,Pyridine ,Materials Chemistry ,Density functional theory ,Physical and Theoretical Chemistry - Abstract
Three new chiral pyridine-containing oxazoline derivatives with fluorine and perfluoromethyl groups, namely, 2-({2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C21H16F3N3O, 2-({5-fluoro-2-[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C18H17F4N3O, and 2-({2-[(3aR,8aS)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine, C22H16F3N3O, as chiral ligands in metal-catalysed asymmetric reactions, were synthesized and characterized by spectral and X-ray diffraction methods. The conformation of the molecules is influenced by strong N—H...N hydrogen bonding and weak C—H...X(X = O and N) interactions. There are no intermolecular hydrogen bonds in the crystal structures of the analysed compounds. Hirshfeld surface analysis showed that the H...H contacts constitute a high percentage of the intermolecular interactions. The conformational analysis was performed by theoretical calculations using the density functional theory (DFT) method. The mechanism of complex formation in terms of the electron-withdrawing effect of the substituents on the oxazoline ring and the ligand conformation is discussed.
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- 2021
26. Reinvestigation of the reaction of 3-substituted 1,2,4-triazines with nitronate anions: unexpected behavior of 3-(2-ethoxyphenyl)-1,2,4-triazine in the reaction with anions of nitroalkanes
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Mariusz Mojzych, Zofia Bernat, and Zbigniew Karczmarzyk
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010405 organic chemistry ,Hydrogen bond ,Organic Chemistry ,Substituent ,010402 general chemistry ,Ring (chemistry) ,Oxime ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Intramolecular force ,Nucleophilic substitution ,Nitronate ,Triazine - Abstract
3-Substituted 1,2,4-triazines easily react with nitronate anions to replace hydrogen atom in the position C-5 according to nucleophilic substitution mechanism and form appropriate oximes of 5-formyl- or 5-acyl-1,2,4-triazines. Present study has shown that the course of the reaction strongly depends on the structure of the substituent in the position C-3 of 1,2,4-triazine ring. Thus, 2-ethoxyphenyl substituent in 1,2,4-triazine allowed to form, besides appropriate oximes, also new nitronic acid derivatives stabilized by intramolecular hydrogen bonds. The synthesis pathway and molecular structures of oximes were confirmed by X-ray analysis performed for model compound 1-[3-(2-ethoxyphenyl)-1,2,4-triazin-5-yl]ethanone oxime. The presence of the new nitronic acid derivatives in the reaction mixture and the theoretical calculations at DFT/B3LYP/6-311++G(d,p) level strongly suggest that intermediate stabilized by bifurcated intramolecular hydrogen bond is a common intermediate for the construction of appropriate oximes.
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- 2019
27. 1,2,4-Triazine Sulfonamides: Synthesis by Sulfenamide Intermediates, In Vitro Anticancer Screening, Structural Characterization, and Molecular Docking Study
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Anna Bielawska, Krzysztof Bielawski, Zbigniew Karczmarzyk, Zofia Urbańczyk-Lipkowska, Danuta Branowska, Maja Morawiak, Waldemar Wysocki, and Ewa Wolińska
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Protein Conformation, alpha-Helical ,Stereochemistry ,Cell Survival ,Sulfenamide ,Pharmaceutical Science ,Antineoplastic Agents ,01 natural sciences ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,lcsh:Organic chemistry ,Cell Line, Tumor ,sulfonamides ,Drug Discovery ,Molecule ,Moiety ,Humans ,Protein Interaction Domains and Motifs ,Physical and Theoretical Chemistry ,skin and connective tissue diseases ,Triazine ,Cell Proliferation ,Binding Sites ,010405 organic chemistry ,Chemistry ,Triazines ,Organic Chemistry ,Estrogen Receptor alpha ,conformational analysis ,Biological activity ,molecular docking ,In vitro ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,anticancer activity ,Chemistry (miscellaneous) ,Drug Design ,MCF-7 Cells ,Molecular Medicine ,Chlorambucil ,Pharmacophore ,Drug Screening Assays, Antitumor ,Estrogen receptor alpha ,Protein Binding ,X-ray analysis - Abstract
In this study, we synthesized novel sulfonamides with a 1,2,4-triazine moiety according to pharmacophore requirements for biological activity. All the synthesized compounds were tested in vitro to verify whether they exhibited anticancer activity against the human breast cancer cell lines MCF-7 and MDA-MB-231. Among them, two most active ones, having IC50 values of 50 and 42 µ, M, respectively, were found to show higher anticancer activity than chlorambucil used as the reference in the in vitro tests. In addition, two other compounds, which had IC50 values of 78 and 91 µ, M, respectively, exhibited a similar level of activity as chlorambucil. X-ray analysis carried out for two of the compounds confirmed their synthesis pathway as well as their assumed molecular structures. Furthermore, a conformational analysis was performed, and electronic parameters of molecules were characterized using theoretical calculations at AM1 and DFT level. Moreover, molecular docking revealed the mode of binding of the investigated 1,2,4-triazine sulfonamides with the human estrogen receptor alpha (ER&alpha, ).
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- 2020
28. Synthesis, Structural Characterization, and Biological Activity of New Pyrazolo[4,3-e][1,2,4]triazine Acyclonucleosides
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Joanna Matysiak, Andrzej Fruziński, Zofia Bernat, Mariusz Mojzych, and Zbigniew Karczmarzyk
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Stereochemistry ,In silico ,Synthetic membrane ,Pharmaceutical Science ,pyrazolo[4,3-e][1,2,4]triazine ,02 engineering and technology ,Analytical Chemistry ,lcsh:QD241-441 ,03 medical and health sciences ,chemistry.chemical_compound ,0302 clinical medicine ,theoretical calculation ,lcsh:Organic chemistry ,Drug Discovery ,Physical and Theoretical Chemistry ,X ray analysis ,Triazine ,Kinase ,Organic Chemistry ,acyclonucleosides ,Biological activity ,molecular docking ,021001 nanoscience & nanotechnology ,anticancer activity ,chemistry ,Chemistry (miscellaneous) ,030220 oncology & carcinogenesis ,Lipophilicity ,Molecular Medicine ,0210 nano-technology ,Human cancer ,X-ray analysis - Abstract
A series of new pyrazolo[4,3-e][1,2,4]triazine acyclonucleosides 2&ndash, 5 and 8 were prepared and evaluated for their anticancer activity against human cancer cell lines (MCF-7, K-562) and CDK2/E, as well as Abl protein kinases inhibitors. Lipophilicity of the compounds was determined using C-18 and immobilized artificial membrane (IAM) chromatography. In order to confirm the molecular structures and synthesis pathway of new acyclonucleosides, X-ray analysis was performed for model compound 3. Theoretical calculations at the DFT/B3LYP/6-311++G(d,p) level were used for the characterization of electronic structures of 1&ndash, 8. The potential antiviral activity of acyclonucleosides 2&ndash, 8 was tested in silico using molecular docking method.
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- 2020
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29. Design, synthesis, structure elucidation and in vitro antiviral and antimicrobial evaluation
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Anna Malm, Katarzyna Stepaniuk, Waldemar Wysocki, Łukasz Świątek, Zbigniew Karczmarzyk, Anna Biernasiuk, Anna Pachuta-Stec, Barbara Rajtar, Monika Pitucha, and Małgorzata Polz-Dacewicz
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0301 basic medicine ,chemistry.chemical_classification ,General Chemistry ,Carbon-13 NMR ,Antimicrobial ,Combinatorial chemistry ,In vitro ,03 medical and health sciences ,Ethyl bromoacetate ,chemistry.chemical_compound ,030104 developmental biology ,Dicarboxylic acid ,Design synthesis ,chemistry ,Antiviral screening ,Cytotoxicity - Abstract
In this study, we described the synthesis of the derivatives of thiosemicarbazide, dicarboximide, 1,2,4-triazole-5-thione and 4-oxo-1,3-thiazolidine. Two different dicarboxylic acid anhydrides reacted with 4-substituted-3-thiosemicarbazide, and derivatives of thiosemicarbazide and dicarboximide were obtained. Next, cyclization reaction of dicarboximide derivatives in alkaline media was used to prepare 1,2,4-triazole-5-thione. The 4-oxo-1,3-thiazolidine was synthesized by the reaction of dicarboximide with ethyl bromoacetate. All obtained derivatives were analysed by 1H and 13C NMR spectra, and for one compound, the X-ray crystallography was done. Antimicrobial, antiviral and in vitro evaluations of cytotoxicity were examined. According to the preliminary antiviral screening, compounds 3 and 4 presented the antiviral activity against HSV-1 and CVB3. Additionally, compound 3 shows selective in vitro toxic effect against human epithelial cells FaDu, without affecting normal animal cell line (Vero). The same derivatives 3 and 4 also displayed a wide spectrum of antimicrobial activity against reference microorganisms and indicated both antibacterial and antifungal potential activities.
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- 2018
30. Synthesis and optical properties of some 3,4-(ethylenedioxythiophen-2-yl)-1,2,4-triazine derivatives
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Michał Gil, Waldemar Wysocki, Agnieszka Woźna, Monika Świętochowska, Zbigniew Karczmarzyk, Przemysław Kalicki, Zofia Urbańczyk-Lipkowska, Danuta Branowska, Ewa Olender, and Iwona Cichosz
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Organic Chemistry ,chemistry.chemical_element ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Stille reaction ,chemistry.chemical_compound ,chemistry ,Computational chemistry ,Drug Discovery ,Thiophene ,Organic chemistry ,Molecule ,Emission spectrum ,Absorption (chemistry) ,0210 nano-technology ,Triazine ,Palladium - Abstract
A series of a hybrid oligomers with different combinations of thiophene, EDOT and 1,2,4-triazine rings have been synthesized and characterized. The synthesis of these alternated 1,2,4-triazine derivatives is reported using a straightforward palladium mediated Stille coupling reaction of 2-tri-n-butyltin-3,4-ethylenedioxythiophene with 3-methylsulfanyl-1,2,4-triazine. The molecular structure and the potential optoelectronic properties of the newly obtained compounds were characterized by UV–Vis absorption and emission spectra, X-ray analysis and theoretical calculations at the DFT level.
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- 2017
31. Synthesis, Structural Characterization, and Biological Activity of New Pyrazolo[4,3
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Mariusz, Mojzych, Zofia, Bernat, Zbigniew, Karczmarzyk, Joanna, Matysiak, and Andrzej, Fruziński
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Chromatography ,Molecular Structure ,Cell Survival ,Triazines ,acyclonucleosides ,Antineoplastic Agents ,Membranes, Artificial ,Nucleosides ,molecular docking ,Article ,Molecular Docking Simulation ,pyrazolo[4,3-e][1,2,4]triazine ,Structure-Activity Relationship ,anticancer activity ,theoretical calculation ,Cell Line, Tumor ,MCF-7 Cells ,Humans ,Cell Proliferation ,X-ray analysis - Abstract
A series of new pyrazolo[4,3-e][1,2,4]triazine acyclonucleosides 2–5 and 8 were prepared and evaluated for their anticancer activity against human cancer cell lines (MCF-7, K-562) and CDK2/E, as well as Abl protein kinases inhibitors. Lipophilicity of the compounds was determined using C-18 and immobilized artificial membrane (IAM) chromatography. In order to confirm the molecular structures and synthesis pathway of new acyclonucleosides, X-ray analysis was performed for model compound 3. Theoretical calculations at the DFT/B3LYP/6-311++G(d,p) level were used for the characterization of electronic structures of 1–8. The potential antiviral activity of acyclonucleosides 2–8 was tested in silico using molecular docking method.
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- 2019
32. Synthesis, structural characterization and biological activity of new pyrazolo[4,3-e][1,2,4]triazine acyclonucleosides
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Mariusz Mojzych, Andrzej Fruziński, Zbigniew Karczmarzyk, and Joanna Matysiak
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chemistry.chemical_compound ,chemistry ,Kinase ,Stereochemistry ,In silico ,Lipophilicity ,Biological activity ,X ray analysis ,Human cancer ,Triazine - Abstract
A series of new pyrazolo[4,3-e][1,2,4]triazine acyclonucleosides 2-5 and 8 were prepared and evaluated for their anticancer activity against human cancer cell lines (MCF-7, K-562) and CDK2/E as well as Abl protein kinases inhibitors. Lipophilicity of the compounds was determined using C-18 and IAM chromatography. In order to confirm molecular structures and synthesis pathway of new acyclonucleosides X-ray analysis was performed for model compound 3. Theoretical calculations at DFT/B3LYP/6-311++G(d,p) level were used for characterization electronic structures of 1–8. The potential antiviral activity of acyclonucleoside 2–8 was tested in silico using molecular docking method.
- Published
- 2019
33. Synthesis, In Vitro Screening and Docking Studies of New Thiosemicarbazide Derivatives as Antitubercular Agents
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Marta Swatko-Ossor, Zbigniew Karczmarzyk, Andrzej Fruziński, Kamil Chudzik, Monika Pitucha, Maciej Wos, Grazyna Ginalska, and Waldemar Wysocki
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Models, Molecular ,synthesis ,Stereochemistry ,Carboxylic acid ,Antitubercular Agents ,Pharmaceutical Science ,Quantitative Structure-Activity Relationship ,Molecular Dynamics Simulation ,Hydrazide ,thiosemicarbazide ,01 natural sciences ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,Mycobacterium tuberculosis ,chemistry.chemical_compound ,Minimum inhibitory concentration ,lcsh:Organic chemistry ,Glutamine synthetase ,Drug Discovery ,Physical and Theoretical Chemistry ,chemistry.chemical_classification ,Binding Sites ,biology ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Hydrogen Bonding ,molecular docking ,biology.organism_classification ,In vitro ,0104 chemical sciences ,Semicarbazides ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,chemistry ,tuberculosis ,Chemistry (miscellaneous) ,Docking (molecular) ,Molecular Medicine ,Drug Screening Assays, Antitumor ,Mycobacterium ,X-ray analysis ,Protein Binding - Abstract
A series of thiosemicarbazide derivatives was designed and synthesized by reaction of carboxylic acid hydrazide with isothiocyanates. The molecular structures of the investigated thiosemicarbazides were confirmed and characterized by spectroscopic analysis. The conformational preference of carbonylthiosemicarbazide chain and intra- and intermolecular interactions in the crystalline state were characterized using X-ray analysis. The antituberculosis activity of the target compounds were tested in vitro against four Mycobacterium strains: M. H37Ra, M. phlei, M. smegmatis, M. timereck. The most active compounds were those with 2-pyridine ring. They exhibited lower minimal inhibitory concentration (MIC) values in the range 7.81&ndash, 31.25 &mu, g/mL in comparison to the other isomers. Compound 5 had activity against M. smegmatis at a concentration of 7.81 &mu, g/mL whereas compound 2 had activity against all tested strains at a concentration of 15.625 &mu, g/mL. The molecular docking studies were performed for investigated compounds using the Mycobacterium tuberculosis glutamine synthetase MtGS as their molecular target.
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- 2019
34. Influence of Complexation of Thiosemicarbazone Derivatives with Cu (II) Ions on Their Antitumor Activity against Melanoma Cells
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Agnieszka Czylkowska, Monika Drozd, Grzegorz Adamczuk, Emilia Fornal, Zbigniew Karczmarzyk, Monika Pitucha, Joanna Kubik, Ewelina Humeniuk, Waldemar Wysocki, Bartłomiej Rogalewicz, Paulina Bartnik, Magdalena Iwan, and Agnieszka Korga-Plewko
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synthesis ,Molecular Conformation ,Apoptosis ,01 natural sciences ,Coordination complex ,lcsh:Chemistry ,thiosemicarbazone ,chemistry.chemical_compound ,Coordination Complexes ,Cytotoxicity ,lcsh:QH301-705.5 ,Spectroscopy ,chemistry.chemical_classification ,Temperature ,General Medicine ,Computer Science Applications ,Gene Expression Regulation, Neoplastic ,anticancer activity ,Thiosemicarbazones ,Cell Survival ,X-ray investigation ,DNA damage ,Antineoplastic Agents ,010402 general chemistry ,Article ,Catalysis ,Inorganic Chemistry ,Inhibitory Concentration 50 ,Necrosis ,Cell Line, Tumor ,TG-DTG techniques ,melanoma ,Humans ,RNA, Messenger ,Physical and Theoretical Chemistry ,Cell Shape ,Molecular Biology ,Semicarbazone ,Ions ,010405 organic chemistry ,Organic Chemistry ,Hydrogen Bonding ,In vitro ,0104 chemical sciences ,copper(II) complex ,Enzyme ,lcsh:Biology (General) ,lcsh:QD1-999 ,chemistry ,Copper ,DNA ,Nuclear chemistry - Abstract
A series of thiosemicarbazone derivatives was prepared and their anti-tumor activity in vitro was tested. The X-ray investigation performed for compounds T2, T3 and T5 confirmed the synthesis pathway and assumed molecular structures of analyzed thiosemicarbazones. The conformational preferences of the thiosemicarbazone system were characterized using theoretical calculations by AM1 method. Selected compounds were converted into complexes of Cu (II) ions. The effect of complexing on anti-tumor activity has been investigated. The copper(II) complexes, with Schiff bases T1, T10, T12, T13, and T16 have been synthesized and characterized by chemical and elemental analysis, FTIR spectroscopy and TGA method. Thermal properties of coordination compounds were studied using TG-DTG techniques under dry air atmosphere. G361, A375, and SK-MEL-28 human melanoma cells and BJ human normal fibroblast cells were treated with tested compounds and their cytotoxicity was evaluated with MTT test. The compounds with the most promising anti-tumour activity were then selected and their cytotoxicity was verified with cell cycle analysis and apoptosis/necrosis detection. Additionally, DNA damages in the form of a basic sites presence and the expression of oxidative stress and DNA damage response genes were evaluated. The obtained results indicate that complexation of thiosemicarbazone derivatives with Cu (II) ions improves their antitumor activity against melanoma cells. The observed cytotoxic effect is associated with DNA damage and G2/M phase of cell cycle arrest as well as disorders of the antioxidant enzymes expression.
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- 2021
35. Synthesis and electrochemical characterization of oligothiophenes with 1,2,4-triazine and 5,5′-bi-1,2,4-triazine as strong electron acceptor units
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Zofia Urbańczyk-Lipkowska, Danuta Branowska, Waldemar Wysocki, Przemysław Kalicki, Zbigniew Karczmarzyk, Barbara Miroslaw, Ilona Bancerz, Przemyslaw Ledwon, Mieczyslaw Lapkowski, and Ewa Olender
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chemistry.chemical_classification ,General Chemical Engineering ,02 engineering and technology ,Electron acceptor ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Electrochemistry ,Photochemistry ,01 natural sciences ,0104 chemical sciences ,law.invention ,chemistry.chemical_compound ,Delocalized electron ,chemistry ,law ,Electron affinity ,Thiophene ,Moiety ,Physical chemistry ,0210 nano-technology ,Electron paramagnetic resonance ,Triazine - Abstract
Two series of 1,2,4-triazine and 5,5′-bi-1,2,4-triazine-based oligothiophene derivatives have been developed and their molecular structures were confirmed by X-ray analysis. Electrochemical, spectroelectrochemical and spectral measurement were used to estimate their properties. The results show that the optical and electronic properties can be tuned over a broad range. The conjugation of two 1,2,4-triazine units leads to a significant strengthening of their electron-accepting properties in contrary to some widely used electron-acceptor units. The comparison of electrochemically estimated and DFT calculated electron affinity (EA) of oligothiophenes with 5,5′-bi-1,2,4-triazine and 1,2,4-triazine units indicates that conjugation of two triazine units leads to the formation of strong electron acceptor moiety with electrochemically estimated EA equal to 4 eV. Electron paramagnetic resonance spectra recorded during electrochemical reduction reveals the delocalization of radical mainly at 5,5′-bi-1,2,4-triazine core in contrary to 1,2,4‐triazine derivatives where thiophene arm is also involved. DFT calculations support the experimental results. These results indicate that obtained materials especially with 5,5′-bi-1,2,4-triazine units can be tested as n-type semiconductors for wide range of organic optoelectronic applications.
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- 2016
36. Structural characterization of copper complexes with chiral 1,2,4-triazine-oxazoline ligands
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Waldemar Wysocki, Zbigniew Karczmarzyk, and Ewa Wolińska
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010405 organic chemistry ,Chemistry ,Organic Chemistry ,Enantioselective synthesis ,chemistry.chemical_element ,Oxazoline ,010402 general chemistry ,01 natural sciences ,Copper ,0104 chemical sciences ,Characterization (materials science) ,chemistry.chemical_compound ,Polymer chemistry ,Triazine - Abstract
The crystal structure determination of oxazoline-1,2,4-triazine ligand 1f and pyridine-oxazoline ligand 2g was used to analyze their conformational preferences when forming complexes with metals. Proton nuclear magnetic resonance (1H NMR), electrospray ionization mass spectrometry and UV-vis spectroscopy as well as theoretical calculation using molecular mechanics (MM) were adopted to study the composition and geometry of oxazoline-1,2,4-triazine ligands 1 complexes with copper(II) acetate monohydrate. The study revealed that during the complexation, (i) Cu(II) ion is reduced to Cu(I) upon the ligand-to-metal charge transfer transition and (ii) the ligands form with copper(I) 2:1 (L:Cu) complexes of tetrahedral geometry. On the basis of the findings, the catalytic cycle and the active transition state for the enantioselective nitroaldol reaction (the Henry reaction) catalyzed by 1–Cu are proposed.
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- 2016
37. Synthesis of unsymmetrical disulfanes bearing 1,2,4-triazine scaffold and their in vitro screening towards anti-breast cancer activity
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Ewa Wolińska, Anna Bielawska, Krzysztof Bielawski, Mariusz Sobiczewski, Danuta Branowska, Alicja Perzyna, Zbigniew Karczmarzyk, Barbara Miroslaw, Waldemar Wysocki, Ewa Olender, and Justyna Ławecka
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Disulfanes ,Original Paper ,biology ,010405 organic chemistry ,Stereochemistry ,Hydrogen bond ,Substituent ,Active site ,General Chemistry ,Dihedral angle ,010402 general chemistry ,01 natural sciences ,X-ray structure determination ,Anticancer activity ,0104 chemical sciences ,chemistry.chemical_compound ,Conformational analysis ,chemistry ,Molecular docking ,biology.protein ,Molecule ,MTT assay ,Estrogen receptor alpha ,Triazine - Abstract
A new series of 1,2,4-triazine unsymmetrical disulfanes were prepared and evaluated as anticancer activity compounds against MCF-7 human breast cancer cells with some of them acting as low micromolar inhibitors. Evaluation of the cytotoxicity using an MTT assay, the inhibition of [3H]-thymidine incorporation into DNA demonstrated that these products exhibit cytotoxic effects on breast cancer cells in vitro. The most effective compounds with 59 and 60 µM compared to chlorambucil with 47 µM were disulfanes bearing methyl and methoxy substituent in an aromatic ring. Furthermore, all new 14 compounds were obtained with 22–74% yield via mild and efficient synthesis of the sulfur–sulfur bond formation from thiols and symmetrical disulfanes using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The molecular structure of the newly obtained compounds was confirmed by X-ray analysis. The conformational preferences of disulfide system were characterized using theoretical calculations at DFT level and statistical distributions of C–S–S–C torsion angle values based on the Cambridge Structural Database (CSD). The DFT calculations and CSD searching show two preferential conformations for C–S–S–C torsion angle close to ± 90° and relatively large freedom of rotation on S–S bond in physiological conditions. The molecular docking studies were performed using the human estrogen receptor alpha (ERα) as molecular target to find possible binding orientation and intermolecular interactions of investigated disulfanes within the active site of ERα. The S…H–S and S…H–C hydrogen bonds between sulfur atoms of bisulfide bridge and S–H and C–H groups of Cys530 and Ala350 as protein residues play crucial role in interaction with estrogen receptor for the most anticancer active disulfane. Graphical abstract Electronic supplementary material The online version of this article (10.1007/s00706-018-2206-y) contains supplementary material, which is available to authorized users.
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- 2018
38. Synthesis, Structure and Antiproliferative Activity of New pyrazolo[4,3- e]triazolo[4,5-b][1,2,4]triazine Derivatives
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Artur Wozny, Mariusz Mojzych, Zbigniew Karczmarzyk, Wojciech Rzeski, Andrzej Fruziński, Małgorzata Juszczak, and Paweł Tarasiuk
- Subjects
Models, Molecular ,Plant growth ,Stereochemistry ,Antineoplastic Agents ,Crystallography, X-Ray ,01 natural sciences ,Structure-Activity Relationship ,chemistry.chemical_compound ,Biological property ,Drug Discovery ,Tumor Cells, Cultured ,medicine ,Humans ,MTT assay ,IC50 ,Cell Proliferation ,Triazine ,Cisplatin ,chemistry.chemical_classification ,Dose-Response Relationship, Drug ,Molecular Structure ,Triazines ,010405 organic chemistry ,Chemistry ,Triazoles ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Cancer cell ,Drug Screening Assays, Antitumor ,medicine.drug ,Tricyclic - Abstract
Background Triazoles and their fused derivatives are an important class of compounds that exhibit interesting biological properties, such as antiasthmatic, antimicrobial, antifungal, analgesic, antiallergic, antiinflammatory, herbicidal, plant growth regulative activity, and anti-HIV-1 activities. Moreover, anticancer activity of 1,2,4-triazole containing derivatives has been documented. Due to the fact a convenient approach toward polycyclic frameworks containing fused 1,2,4-triazoles was described. Objective The objective of this article is the synthesis of new pyrazolo[4,3-e]triazolo[4,5- b][1,2,4]triazine derivatives with potential antiproliferative activity. Methods Cancer cell proliferation was analysed by means of MTT assay after 96 h treatment. IC50 was calculated using computerized linear regression analysis of quantal log doseprobit functions, according to the method of Litchfield and Wilcoxon. X-ray data were collected on the Bruker SMART APEX II CCD diffractometer; The structure was solved by direct methods using SHELXS-2013 and refined by full-matrix least-squares with SHELXL-2014/7. All calculations were performed using WINGX version 2014.1 package. Results The series of pyrazolo[4,3-e]triazolo[4,5-b][1,2,4]triazine derivatives were synthesized. MTT assay revealed that the compounds inhibited cancer cells growth at concentrations below 10 µM. The tested compounds showed higher antiproliferative activity than popular cytostatics cisplatin (lung carcinoma) and 5-fluorouracil (colon adenocarcinoma). X-ray examinations showed that final products in the crystalline phase have a linear form. Conclusion In the paper we have reported the synthesis and spectroscopic analysis of new condensed tricyclic derivatives of the pyrazolo[4,3-e]triazolo[4,5-b][1,2,4]triazine. MTT analysis revealed concentration-dependent decrease in lung A549 and colon LS180 cancer cells proliferation. In order to explain the molecular mechanisms involved in anticancer activity of pyrazolo[4,3- e]triazolo[4,5-b][1,2,4]triazine derivatives, our research will be continued.
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- 2018
39. Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity
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Agnieszka A. Kaczor, Waldemar Wysocki, Zbigniew Karczmarzyk, Dariusz Matosiuk, Sylwia Andrzejczuk, Maja Morawiak, Tomasz M. Wróbel, Zofia Urbańczyk-Lipkowska, and Urszula Kosikowska
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Models, Molecular ,Antifungal ,Antifungal Agents ,synthesis ,medicine.drug_class ,Stereochemistry ,Molecular Conformation ,Pharmaceutical Science ,Imidazoline receptor ,Moderate activity ,Microbial Sensitivity Tests ,Imidazoline derivatives ,Molecular Dynamics Simulation ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Candida albicans ,Drug Discovery ,medicine ,Clotrimazole ,Physical and Theoretical Chemistry ,Imidazolines ,Mode of action ,14-α-sterol demethylase ,biology ,Organic Chemistry ,Hydrogen Bonding ,biology.organism_classification ,molecular modelling ,chemistry ,Chemistry (miscellaneous) ,Molecular Medicine ,antifungal ,Derivative (chemistry) ,Fluconazole ,Isocyanates ,X-ray analysis ,medicine.drug - Abstract
Six novel imidazoline derivatives were synthesized and tested in antifungal assays. One of the compounds, N-cyclohexyl-2-imino-3-(4-nitrophenyl)imidazolidine-1-carboxamide showed moderate activity against several clinical strains of Candida albicans. Its structure was solved by X-ray crystallography and its mode of action was deduced using molecular modelling. It was found to be similar to that of fluconazole. The potential for further optimization including SAR of the compound is briefly discussed.
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- 2015
40. Structural investigations of a series of 1,6-aryl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-ones with potential antinociceptive activity
- Author
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Marzena Rządkowska, Zbigniew Karczmarzyk, Zofia Urbańczyk-Lipkowska, Elżbieta Szacoń, Dariusz Matosiuk, Waldemar Wysocki, and Przemysław Kalicki
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education.field_of_study ,Hydrobromide ,Hydrogen bond ,Chemistry ,Organic Chemistry ,Population ,Crystal structure ,Keto–enol tautomerism ,Carbon-13 NMR ,Tautomer ,Analytical Chemistry ,Inorganic Chemistry ,Crystallography ,Computational chemistry ,Molecule ,education ,Spectroscopy - Abstract
The structural investigations of a series of new bioactive imidazo[1,2-a]pyrimidines 1–6 were undertaken using IR, 1H and 13C NMR spectroscopic analysis, X-ray crystal structure determinations and theoretical calculations. The compounds 1–6 were obtained by condensation of the respective 1-aryl-4,5-dihydro-1H-imidazol-2-amine hydrobromide and diethyl phenylmalonate in presence of sodium methoxide in methanol and for these compounds the equilibrium between possible O10-enol/O11-keto (a), O11-enol/O10-keto (b) and O10,O11-diketo (c) tautomeric forms were investigated in the gaseous phase, solution and crystalline state. Spectroscopic studies 1H, 13C NMR and IR allowed for the identification of the compounds 1–6 but they did not indicate explicitly their tautomeric forms present in solution and in the solid state. The X-ray analysis showed that the molecules of all investigated compounds exist as the O10-enol/O11-keto (a) tautomeric form in the crystalline state. The hydroxyl and carbonyl groups characteristic for existing tautomeric form are involved in a strong intra- and/or intermolecular O H⋯O and O H⋯N hydrogen bonds. The theoretical calculations at DFT/B3LYP/6-311++G(d,p) level showed that two tautomeric forms (a) and (c) can coexist both in gas phase and the solution with the population of them being in the relation (a) > (or ≫) (c). The comparison of the experimentally recorded IR, 1H and 13C spectra with the corresponding spectra theoretically calculated for all possible tautomeric forms of 1–6 shows that the correlation of experimental and theoretical spectra can be used to a limited extent for the identification of tautomeric forms.
- Published
- 2015
41. Discovery of nitroaryl urea derivatives with antiproliferative properties
- Author
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Zbigniew Karczmarzyk, Agnieszka A. Kaczor, Aneta Grabarska, Andrzej Fruziński, Waldemar Wysocki, Andrzej Stepulak, Michał Kiełbus, Dariusz Matosiuk, Vladimír Kryštof, Sylwia K Król, and Tomasz M. Wróbel
- Subjects
0301 basic medicine ,Stereochemistry ,Antineoplastic Agents ,01 natural sciences ,Structure-Activity Relationship ,03 medical and health sciences ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,medicine ,Humans ,Urea ,Structure–activity relationship ,Moiety ,Cytotoxicity ,Protein Kinase Inhibitors ,Cell Proliferation ,Pharmacology ,Cisplatin ,Dose-Response Relationship, Drug ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Drug discovery ,Cyclin-Dependent Kinase 2 ,General Medicine ,0104 chemical sciences ,030104 developmental biology ,Biochemistry ,Cancer cell ,Drug Screening Assays, Antitumor ,CDK inhibitor ,medicine.drug - Abstract
A series of urea derivatives bearing nitroaryl moiety has been synthesized and assayed for their potential antiproliferative activities. Some of the tested compounds displayed activity in RK33 laryngeal cancer cells and TE671 rhabdomyosarcoma cells while being generally less toxic to healthy HSF human fibroblasts cells. One compound was demonstrated to be a moderate CDK2 inhibitor with IC50 = 14.3 µM. Its structure was solved by an X-ray crystallography and molecular modelling was performed to determine structure-activity relationship. Obtained compounds constitute novel structures and generally demonstrated greater cytotoxicity in comparison to cisplatin. This study offers new structural motifs with potential for further development.
- Published
- 2015
42. Synthesis, photophysics and electrochemical properties of 1,1′-(2,2′-bithiophene-5,5′-diyl)bis(cycloalkeno[c]pyridine) as a result of the Diels–Alder reaction of 3-(2-thienyl)-1,2,4-triazine
- Author
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Mieczyslaw Lapkowski, Justyna Ławecka, Ewa Olender, Bartosz Chaciak, Przemyslaw Ledwon, Waldemar Wysocki, Zbigniew Karczmarzyk, and Danuta Branowska
- Subjects
chemistry.chemical_element ,General Chemistry ,Photochemistry ,Medicinal chemistry ,Catalysis ,Coupling reaction ,chemistry.chemical_compound ,chemistry ,Pyridine ,Materials Chemistry ,Thiophene ,Cyclic voltammetry ,Cycloheptane ,Palladium ,Triazine ,Diels–Alder reaction - Abstract
Two π-conjugated thienylenecycloalkeno[c]pyridine (A–D)2 (cyclopentane, 1, and cycloheptane, 2, units when n = 1 and 3, respectively) compounds were prepared using a palladium C–C coupling reaction. The π–π* absorption peak of compound 1 was observed at the longer wavelength of 392 nm than that of compound 2, which was observed at 364 nm. UV-Vis data reflect the interaction between the thiophene ring (donor – D) and cycloalkeno[c]pyridine (acceptor – A) units. These compounds show photoluminescence (PL) in the range of 466–470 nm and give quantum yields, Φ, of 15%. Furthermore, intermediates 5 and 6 are characterized by their shorter absorption peaks (304 and 292 nm, respectively). The electrochemical parameters of compounds 1 and 2 were characterized using cyclic voltammetry (CV) measurements and theoretical calculations at the DFT/B3LYP/6-311++G(d,p) level.
- Published
- 2015
43. Synthetic Approaches for Sulfur Derivatives Containing 1,2,4-Triazine Moiety: Their Activity for in Vitro Screening towards Two Human Cancer Cell Lines
- Author
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Zbigniew Karczmarzyk, Przemysław Kalicki, Anna Bielawska, Waldemar Wysocki, Krzysztof Bielawski, Justyna Ławecka, and Zofia Urbańczyk-Lipkowska
- Subjects
Cell Survival ,Stereochemistry ,Molecular Conformation ,Sulfenamide ,chemistry.chemical_element ,Antineoplastic Agents ,Crystallography, X-Ray ,Structure-Activity Relationship ,chemistry.chemical_compound ,Bromide ,Cell Line, Tumor ,Drug Discovery ,Humans ,Moiety ,Structure–activity relationship ,Cytotoxicity ,Triazine ,Triazines ,General Chemistry ,General Medicine ,Sulfur ,In vitro ,chemistry ,MCF-7 Cells ,Quantum Theory - Abstract
A series of sulfur 1,2,4-triazine derivatives were prepared and evaluated as anticancer compounds for two human breast cancer cell lines (MCF-7, MDA-MB-231) with some of them acting as low micromolar inhibitors. Evaluation of the cytotoxicity using a 3-(4,5-dimethylthiazol-2-yl)-3,5-diphenyltetrazolium bromide (MTT) assay, the inhibition of [(3)H]thymidine incorporation into DNA, and collagen synthesis inhibition demonstrated that these products exhibit cytotoxic effects on these breast cancer cell lines in vitro. The most effective were disulfide and sulfenamide compounds with two valence sulfur atoms. A structure-activity relationship study was performed using X-ray analysis and theoretical calculations at an ab initio density functional theory (DFT) level.
- Published
- 2015
44. Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity
- Author
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Dorota Kowalczuk, Zofia Urbańczyk-Lipkowska, Grazyna Ginalska, Maciej Wos, Małgorzata Miazga-Karska, Agnieszka A. Kaczor, Katarzyna Klimek, Maja Morawiak, Zbigniew Karczmarzyk, Waldemar Wysocki, and Monika Pitucha
- Subjects
0301 basic medicine ,Cell division ,Stereochemistry ,Carboxylic acid ,01 natural sciences ,Cell Line ,Nitrophenols ,03 medical and health sciences ,Structure-Activity Relationship ,Multi target ,Humans ,Glycoside Hydrolase Inhibitors ,Cytotoxicity ,Cell Proliferation ,Pharmacology ,chemistry.chemical_classification ,Binding Sites ,Bacteria ,010405 organic chemistry ,Chemistry ,General Medicine ,Hep G2 Cells ,In vitro ,0104 chemical sciences ,Anti-Bacterial Agents ,Semicarbazides ,Glucose binding ,Molecular Docking Simulation ,030104 developmental biology ,Enzyme ,Biochemistry ,A549 Cells ,MCF-7 Cells ,Antibacterial activity - Abstract
A series of thiosemicarbazides with 4-nitrophenyl group was obtained in the reaction of carboxylic acid hydrazides with isothiocyanates. All compounds were checked for their antibacterial and antiproliferative activity. Our results have shown that derivatives 6-8 possessed antibacterial activity against S. aureus, S. epidermidis, S. mutans and S. sanguinis, moderate cytotoxicity and good therapeutic safety in vitro. Additionally, compounds 1 and 4 significantly inhibited A549, HepG2 and MCF-7 cell division. Moreover, PASS software indicated that newly obtained compounds are potential α-glucosidase inhibitors. This was confirmed by in vitro studies. To investigate the mode of interaction with the molecular target compounds were docked to glucose binding site of the enzyme and exhibited a similar binding mode as glucose.
- Published
- 2017
45. Valence tautomerism of new pyrazolo[4,3-e]tetrazole[4,5-b][1,2,4]triazines
- Author
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Zofia Urbańczyk-Lipkowska, Zbigniew Karczmarzyk, Waldemar Wysocki, Mariusz Mojzych, and Natalia Żaczek
- Subjects
Valence (chemistry) ,Hydrogen bond ,Organic Chemistry ,Intermolecular force ,Ab initio ,Crystal structure ,Tautomer ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,symbols.namesake ,chemistry ,Computational chemistry ,symbols ,Tetrazole ,van der Waals force ,Spectroscopy - Abstract
New pyrazolo[4,3-e]tetrazolo[4,5-b][1,2,4]triazines 5 and 6 were prepared as new biological active compounds with potential anticancer activity referring to our previous study. The 1H NMR spectra reveal tautomeric equilibrium azido and tricyclic forms of these compounds in solution. The molecular and crystal structures of 5 and 6 were determined by the X-ray analysis. The X-ray investigations show that in the crystalline state the compounds 5 and 6 exist as the linear tricyclic pyrazolo[4,3-e]tetrazolo[4,5-b][1,2,4]triazine tautomeric form. The analysis of the intra- and intermolecular interactions indicates the weak C–H⋯N hydrogen bonds and π⋯π interactions in crystal of 6 and van der Waals forces only in crystal of 5 as the non-covalent interactions influencing the molecular packing. The theoretical calculations at the ab initio DFT/B3LYP/6-311++G(d,p) level showed the azido form (3 and 4) as one existing in the gaseous phase and the coexistence of the tricyclic linear (5 and 6) and azido tautomeric forms in solution, wherein the contribution of the linear form compared to the azido form changes with polarity of the solvent.
- Published
- 2014
46. A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines
- Author
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Justyna Ławecka, Zofia Urbanczyk-Lipkowska, Ewa Olender, Danuta Branowska, Waldemar Wysocki, Zbigniew Karczmarzyk, and Przemysław Kalicki
- Subjects
Nucleophile ,Chemistry ,Organic Chemistry ,Disulfide bond ,Medicinal chemistry ,Combinatorial chemistry ,Displacement (fluid) ,Ion - Abstract
Nucleophilic displacement of chlorides in 3,3′-dichloro-5,5′-bi-1,2,4-triazine with benzenethiolate or 2-pyridinethiolate anion afforded the corresponding symmetrical disulfide of 5,5′-bi-1,2,4-triazine in high yields. These products were transformed into 6,6′-bis(phenylthio)-2,2′-bipyridines and 6,6′-bis(2-pyridylthio)-2,2′-bipyridines by using Diels-Alder reactions. All compounds were fully characterized by spectroscopic methods and the X-ray diffraction analysis.
- Published
- 2014
47. Experimental and computational studies on the tautomerism of N-substituted 3-amino-5-oxo-4-phenyl-1H-pyrazolo-1-carboxamides with antibacterial activity
- Author
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Tomasz M. Wróbel, Dariusz Matosiuk, Ewaryst Mendyk, Antti Poso, Zbigniew Karczmarzyk, Waldemar Wysocki, Agnieszka A. Kaczor, and Monika Pitucha
- Subjects
chemistry.chemical_classification ,Stereochemistry ,Hydrogen bond ,Organic Chemistry ,Carbon-13 NMR ,Tautomer ,Analytical Chemistry ,Inorganic Chemistry ,Enzyme ,chemistry ,Group (periodic table) ,Pyrazolones ,Antibacterial activity ,Two-dimensional nuclear magnetic resonance spectroscopy ,Spectroscopy - Abstract
The tautomerism of N-substituted 3-amino-5-oxo-4-phenyl-1H-pyrazolo-1-carboxamides with antibacterial activity is studied with X-ray crystallography, IR, 1H and 13C NMR (including NOESY spectra) and quantum chemical calculations. It is found that the form with the keto group at position 5 is the preferred one in the crystalline state and in DMSO, although some fraction with the corresponding hydroxy group also occurs in both states. This finding was related to the antibacterial activity of the studied compounds as the energetic stabilization of the keto group may determine their proper hydrogen bond interactions with the bacterial enzyme.
- Published
- 2013
48. Synthesis of novel isothiazolopyridines and their in vitro evaluation against Mycobacterium and Propionibacterium acnes
- Author
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Małgorzata Śliwińska, Zbigniew Karczmarzyk, Wiesław Malinka, Andrzej Fruziński, Piotr Świątek, Bogumiła Szponar, and Andrzej Gamian
- Subjects
Cell Survival ,Pyridines ,Clinical Biochemistry ,Antitubercular Agents ,Molecular Conformation ,Pharmaceutical Science ,Microbial Sensitivity Tests ,Antimycobacterial agents ,Crystallography, X-Ray ,Biochemistry ,Mycobacterium ,Microbiology ,Structure-Activity Relationship ,Synthesis ,chemistry.chemical_compound ,Propionibacterium acnes ,Minimum inhibitory concentration ,Chlorocebus aethiops ,Drug Discovery ,Animals ,Vero Cells ,Molecular Biology ,Medicine(all) ,Isothiazole ,biology ,Chemistry ,Organic Chemistry ,Mycobacterium tuberculosis ,biology.organism_classification ,In vitro ,Thiazoles ,Isothiazolopyridine ,Molecular Medicine ,Mycobacterium fortuitum ,Antibacterial activity ,Growth inhibition - Abstract
In this paper we describe synthesis, structures and some physicochemical properties of 20 isothiazolopyridines 8–13 substituted differently into an isothiazole ring as well as their in vitro antibacterial assays against Mycobacterium tuberculosis H37Rv, Mycobacterium fortuitum PCM 672 and Propionibacterium acnes PCM 2400. Compound 13a was found to be the most active derivative against M. tuberculosis H37Rv, demonstrating 100% growth inhibition of microorganisms in the primary screen (minimum inhibitory concentration [MIC] 6.25μg/mL). Nineteen of the prepared compounds were evaluated against M. fortuitum PCM 672 and P. acnes PCM 2400 and only compounds 9 and 12d exhibited excellent activity against individual strains of microorganisms with MIC90
- Published
- 2013
49. Structural studies on N-(1-naphthyl)-3-amino-5-oxo-4-phenyl-1H-pyrazole-1-carboxamide with antibacterial activity
- Author
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Malgorzata Brodacka, Monika Pitucha, Dariusz Matosiuk, Zbigniew Karczmarzyk, Waldemar Wysocki, Andrzej Fruziński, Tomasz M. Wróbel, and Agnieszka A. Kaczor
- Subjects
medicine.drug_class ,Stereochemistry ,Chemistry ,Organic Chemistry ,medicine ,Carboxamide ,Antibacterial activity ,Biochemistry - Published
- 2013
50. Synthesis and characterization of osmium(II) chlorocarbonyl complexes with bidentate phosphines
- Author
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Waldemar Wysocki, Zbigniew Karczmarzyk, Anna Kamecka, and Andrzej Kapturkiewicz
- Subjects
Denticity ,Chemistry ,Lability ,Inorganic chemistry ,Infrared spectroscopy ,chemistry.chemical_element ,Medicinal chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,X-ray crystallography ,Materials Chemistry ,Molecule ,Osmium ,Physical and Theoretical Chemistry ,Luminescence ,Benzene - Abstract
Simple reactions of K2OsCl6 with a cis-1,2-bis(diphenylphosphino)ethene or 1,2-bis(diphenylphosphino)benzene in 1:2.05 ratio performed in refluxing DMF solution lead to the formation of the osmium(II) complexes with formulae of Os(P ∩ P)(CO)2Cl2. The obtained complexes were characterized by means of IR and 31P NMR spectroscopic techniques and their molecular structures were confirmed by X-ray investigations. Due to lability of CO and Cl− within Os(P ∩ P)(CO)2Cl2 molecules both of the investigated complexes can be converted to luminescent [Os(N ∩ N)(P ∩ P)(CO)Cl]+ species.
- Published
- 2013
Catalog
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