13 results on '"Tugrak M"'
Search Results
2. Crystal structure of (E)-2-({4-hydroxy-5-methoxy-3-[(4-methyl-1-piperazinyl)methyl]phenyl} methylidene)-1-indanone, C23H26N2O3
- Author
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Tugrak Mehtap, Aydin Abdullah, Gul Halise Inci, Sahin Ertan, and Akkurt Mehmet
- Subjects
1444431 ,Physics ,QC1-999 ,Crystallography ,QD901-999 - Abstract
C23H26N2O3, triclinic, P1̅ (No. 2), a = 10.6646(19) Å, b = 10.7784(17) Å, c = 11.150(2) Å, α = 67.787(7)°, β = 64.309(7)°, γ = 64.271(7)°, V = 1011.6(3) Å3, Z = 2, Rgt(F) = 0.0502, wRref(F2) = 0.1481, T = 293 K.
- Published
- 2017
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3. Synthesis and in vitro carbonic anhydrases and acetylcholinesterase inhibitory activities of novel imidazolinone-based benzenesulfonamides.
- Author
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Tugrak M, Gul HI, Demir Y, Levent S, and Gulcin I
- Subjects
- Carbonic Anhydrase Inhibitors chemical synthesis, Carbonic Anhydrase Inhibitors chemistry, Cholinesterase Inhibitors chemical synthesis, Cholinesterase Inhibitors chemistry, Humans, Imidazolines chemistry, Molecular Structure, Sulfonamides chemical synthesis, Sulfonamides chemistry, Benzenesulfonamides, Acetylcholinesterase metabolism, Carbonic Anhydrase Inhibitors pharmacology, Carbonic Anhydrases metabolism, Cholinesterase Inhibitors pharmacology, Imidazolines pharmacology, Sulfonamides pharmacology
- Abstract
New imidazolinone-based benzenesulfonamides 3a-e and 4a-e were synthesized in three steps and their chemical structures were confirmed by
1 H NMR (nuclear magnetic resonance),13 C NMR, and high-resolution mass spectrometry. The benzenesulfonamides used were sulfacetamide (3a, 4a), sulfaguanidine (3b, 4b), sulfanilamide (3c, 4c), sulfadiazine (3d, 4d), sulfamerazine (3e), and sulfathiazole (4e). The compounds were evaluated against carbonic anhydrase (CA) and acetylcholinesterase (AChE) enzymes to obtain possible drug candidate/s. The lead compounds of the series were 3a and 4a against human CA (hCA) I, whereas 3d and 4a were leads against hCA II in terms of Ki values. Series 4 includes more effective CAs inhibitors than series 3 (except 3d). Series 4 compounds having a nitro group (except 4d) were 3.3-4.8 times more selective inhibitors than their corresponding analogues 3a-d in series 3, in which hydrogen was located in place of the nitro group, by considering Ki values against hCA II. Compounds 3c and 4c, where the sulfanilamide moiety is available, were the leads in terms of AChE inhibition with the lowest Ki values. The use of secondary sulfonamides was a more effective modification on CA inhibition, whereas the primary sulfonamide was the effective substitution in terms of AChE inhibitory potency., (© 2020 Deutsche Pharmazeutische Gesellschaft.)- Published
- 2021
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4. Synthesis of benzamide derivatives with thiourea-substituted benzenesulfonamides as carbonic anhydrase inhibitors.
- Author
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Tugrak M, Gul HI, Demir Y, and Gulcin I
- Subjects
- Benzamides chemical synthesis, Benzamides chemistry, Carbonic Anhydrase I metabolism, Carbonic Anhydrase II metabolism, Carbonic Anhydrase Inhibitors chemical synthesis, Carbonic Anhydrase Inhibitors chemistry, Dose-Response Relationship, Drug, Humans, Molecular Structure, Structure-Activity Relationship, Sulfonamides chemistry, Thiourea chemistry, Benzamides pharmacology, Carbonic Anhydrase I antagonists & inhibitors, Carbonic Anhydrase II antagonists & inhibitors, Carbonic Anhydrase Inhibitors pharmacology, Sulfonamides pharmacology, Thiourea pharmacology
- Abstract
The novel compounds with the chemical structure of N-({4-[N'-(substituted)sulfamoyl]phenyl}carbamothioyl)benzamide (1a-g) and 4-fluoro-N-({4-[N'-(substituted)sulfamoyl]phenyl}carbamothioyl)benzamide (2a-g) were synthesized as potent and selective human carbonic anhydrase (hCA) I and hCA II candidate inhibitors. The aryl part was changed to sulfacetamide, sulfaguanidine, sulfanilamide, sulfathiazole, sulfadiazine, sulfamerazine, and sulfametazine. The K
i values of compounds 1a-g were in the range of 20.73 ± 4.32 to 59.55 ± 13.07 nM (hCA I) and 5.69 ± 0.43 to 44.81 ± 1.08 nM (hCA II), whereas the Ki values of compounds 2a-g were in the range of 13.98 ± 2.57 to 75.74 ± 13.51 nM (hCA I) and 8.15 ± 1.5 to 49.86 ± 6.18 nM (hCA II). Comparing the Ki values of the final compounds and acetazolamide, compound 1c with the sulfanilamide moiety (Ki = 5.69 ± 0.43 nM, 8.8 times) and 2f with the sulfamerazine moiety (Ki = 8.15 ± 1.5 nM, 6.2 times) demonstrated promising and selective inhibitory effects against the hCA II isoenzyme, the main target protein in glaucoma. Furthermore, compounds 1d (Ki = 20.73 ± 4.32, 4 times) and 2d (Ki = 13.98 ± 2.57, 5.9 times), which have the sulfathiazole moiety, were found as potent hCA I inhibitors. Compounds 1c and 2f can be considered as the lead compounds determined in the present study, which can be investigated further to alleviate glaucoma symptoms., (© 2020 Deutsche Pharmazeutische Gesellschaft.)- Published
- 2021
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5. Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors.
- Author
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Tugrak M, Gul HI, Bandow K, Sakagami H, Gulcin I, Ozkay Y, and Supuran CT
- Subjects
- Apoptosis, Carbonic Anhydrase I antagonists & inhibitors, Carbonic Anhydrase II antagonists & inhibitors, Cell Proliferation, Humans, Molecular Structure, Neoplasms pathology, Structure-Activity Relationship, Tumor Cells, Cultured, Antineoplastic Agents chemical synthesis, Antineoplastic Agents pharmacology, Carbonic Anhydrase Inhibitors chemical synthesis, Carbonic Anhydrase Inhibitors pharmacology, Mannich Bases chemistry, Neoplasms drug therapy, Piperazines chemical synthesis, Piperazines pharmacology
- Abstract
New mono Mannich bases, (2-(4-hydroxy-3-((4-substituephenylpiperazin-1-yl)methyl)benzylidene)-2,3-dihydro-1H-inden-1-one), were prepared to evaluate their cytotoxic/anticancer properties and also their inhibitory effects on human carbonic anhydrase I and II isoenzymes (hCA I and II). Amine part was changed as [N-phenylpiperazine (1), N-benzylpiperazine (2), 1-(2-fluorophenyl)piperazine (3), 1-(4-fluorophenyl)piperazine (4), 1-(2-methoxyphenyl)piperazine (5)]. The structure of the synthesized compounds was characterized by
1 H NMR,13 C NMR and HRMS spectra. Cytotoxicity results of the series pointed out that the compound 4 had the highest tumor selectivity value (TS: 59.4) possibly by inducing necrotic cell death in series. Additionally, all compounds synthesized showed a good inhibition profile towards hCA I and II isoenzymes with the Ki values between 29.6 and 58.4 nM and 38.1-69.7 nM, respectively. These values were lower than the reference compound AZA. However, it seems that the compounds 4 and 2 can be considered as lead compounds of CA studies with the lowest Ki values in series for further designs., (Copyright © 2019 Elsevier Inc. All rights reserved.)- Published
- 2019
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6. New phenolic Mannich bases with piperazines and their bioactivities.
- Author
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Gul HI, Tugrak M, Gul M, Mazlumoglu S, Sakagami H, Gulcin I, and Supuran CT
- Subjects
- Antineoplastic Agents chemistry, Apoptosis, Carbonic Anhydrase Inhibitors chemistry, Cell Proliferation, Drug Screening Assays, Antitumor, Humans, Neoplasms enzymology, Neoplasms pathology, Structure-Activity Relationship, Tumor Cells, Cultured, Antineoplastic Agents pharmacology, Carbonic Anhydrase I antagonists & inhibitors, Carbonic Anhydrase II antagonists & inhibitors, Carbonic Anhydrase Inhibitors pharmacology, Mannich Bases chemistry, Neoplasms drug therapy, Piperazines chemistry
- Abstract
In this study, new Mannich bases, 2-(4-hydroxy-3-methoxy-5-((substitutedpiperazin-1-yl)methyl)benzylidene)-2,3-dihydro-1H-inden-1-one (1, 2, 4, 5, 8), 2-(3-((substituted)piperazin-1-yl)methyl)-4-hydroxy-5-methoxybenzylidene)-2,3-dihydro-1H-inden-1-one (3, 6, 7) were synthesized with the reaction of vanilin derived chalcone compound (2-(4-hydroxy-3-methoxybenzylidene)indan-1-one), paraformaldehyde and suitable amine in 1:1.2:1 mol ratios. Amine part was changed as N-methylpiperazine (1), N-phenylpiperazine (2), N-benzylpiperazine (3), 1-(2-methoxyphenyl)piperazine (4), 1-(3-methoxyphenyl)piperazine (5), 1-(2-fluorophenyl)piperazine (6), 1-(4-fluorophenyl)piperazine (7), and 1-(3-trifluoromethyl)phenyl piperazine (8). Compounds were evaluated in terms of cytotoxic/anticancer and CA inhibitory effects. According to the results obtained, the compounds 2 and 8 had the highest potency selectivity expression (PSE) values (60.6 and 19.2, respectively). On the other hand, the compounds 3 (Ki = 209.6 ± 70.2 pM) and 5 (Ki = 342.66 ± 63.72 pM) had the lowest Ki values in CA inhibition experiments towards hCA I and hCA II, respectively. In conclusion, the compounds 2 (with cytotoxic/anticancer activity), 3 (with hCA I inhibiting activity) and 5 (with hCA II inhibiting activity) can be leading compounds of the study for further designs and evaluations., (Copyright © 2019 Elsevier Inc. All rights reserved.)
- Published
- 2019
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7. New azafluorenones with cytotoxic and carbonic anhydrase inhibitory properties: 2-Aryl-4-(4-hydroxyphenyl)-5H-indeno[1,2-b]pyridin-5-ones.
- Author
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Tugrak M, Inci Gul H, Sakagami H, Gulcin I, and Supuran CT
- Subjects
- Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Carbonic Anhydrase I metabolism, Carbonic Anhydrase II metabolism, Cell Line, Tumor, Cell Survival drug effects, Drug Screening Assays, Antitumor, Humans, Neoplasms drug therapy, Neoplasms enzymology, Pyridines chemistry, Pyridines pharmacology, Carbonic Anhydrase I antagonists & inhibitors, Carbonic Anhydrase II antagonists & inhibitors, Carbonic Anhydrase Inhibitors chemistry, Carbonic Anhydrase Inhibitors pharmacology, Fluorenes chemistry, Fluorenes pharmacology
- Abstract
New azafluorenones, 2-aryl-4-(4-hydroxyphenyl)-5H-indeno[1,2-b]pyridin-5-ones, were prepared to evaluate their cytotoxic/anticancer properties, also their inhibitory effects on hCA I and II isoenzymes. Aryl part was changed as [phenyl (H1), 4-methylphenyl (H2), 4-methoxyphenyl (H3), 4-fluorophenyl (H4), 4-bromophenyl (H5), 4-chlorophenyl (H6), 3-hydroxyphenyl (H7), and 4-hydroxyphenyl (H8)]. The structure of the synthesized compounds was characterized by
1 H NMR,13 C NMR and HRMS spectra. Cytotoxicity results of the series pointed out that the compounds H6 (PSE: 28.0) and H5 (PSE: 27.3), with the highest potency selectivity expression (PSE) value, can be considered as leader compounds of the study in designing novel anticancer agents. Additionally, all azafluorenones synthesized showed a good inhibition profile towards hCA I and II isoenzymes in the range of 54.14-73.72 nM and 67.28-76.15 nM, respectively. The compounds H5 and H6 can be considered for further designs with their cytotoxic and CA inhibitory profiles., (Copyright © 2018. Published by Elsevier Inc.)- Published
- 2018
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8. Synthesis and Cytotoxicities of New Azafluorenones with Apoptotic Mechanism of Action and Cell Cycle Analysis.
- Author
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Gul HI, Tugrak M, Gul M, Sakagami H, Umemura N, and Anil B
- Subjects
- Antineoplastic Agents chemical synthesis, Antineoplastic Agents chemistry, Cell Line, Cell Proliferation drug effects, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Fluorenes chemistry, Humans, Molecular Structure, Structure-Activity Relationship, Antineoplastic Agents pharmacology, Apoptosis drug effects, Cell Cycle drug effects, Fluorenes chemical synthesis, Fluorenes pharmacology
- Abstract
Background: In this study, new azafluorenones, 4-(4-fluorophenyl)-2-(4-substitutedphenyl)-5Hindeno[ 1,2-b] pyridin-5-one, I1-I8 were synthesized and chemical structures were elucidated by spectral analysis. All compounds were reported for the first time here., Method: Compounds were tested in terms of cytotoxicity. They were found as cytotoxins/anticancer compounds., Results: It was found that the lead compounds of the series were I5 and I8 according to SI, TS, PSE calculations. When PSE values were considered, compound I5 having chlorine had the highest PSE value of 126.4. Second highest PSE value of 50.5 belonged to I8, which had thiophene ring in its chemical structure. I8 as a representative compound of the series was forwarded to cell cycle analysis. I8 arrested S phase of the cell cycle and lead to apoptosis by inducing PARP cleavage suggesting that at least one of the mechanisms of cytotoxic action of the series was apoptosis., Conclusion: It was clearly demonstrated that compound I8 can induce early apoptosis at a concentration of 5 µM. The compounds I5 and I8 can be considered as lead compounds of the series with the highest SI, TS, PSE values for further studies., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.)
- Published
- 2018
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9. The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes.
- Author
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Yamali C, Tugrak M, Gul HI, Tanc M, and Supuran CT
- Subjects
- Carbonic Anhydrase I drug effects, Carbonic Anhydrase II drug effects, Carbonic Anhydrase Inhibitors pharmacology, Mannich Bases
- Abstract
Phenolic mono Mannich bases [2-[4-hydroxy-3-(aminomethyl)benzylidene]-2,3-dihydro-1H-inden-1-one (8-15)] and bis Mannich bases [2-[4-hydroxy-3,5-bis(aminomethyl)benzylidene]-2, 3-dihydro-1H-inden-1-one (2-7)] were synthesized starting from 2-(4-hydroxybenzylidene)-2, 3-dihydro-inden-1-one (1). This study was designed in order to investigate the carbonic anhydrase (CA, EC 4.2.1.1) inhibitory properties of a library of compounds incorporating the phenol functional group. All prepared compounds showed a low inhibition percentages on both human (h) isoforms hCA I and hCA II compared to the reference sulfonamide acetazolamide. Mannich bases 2-15 had lower inhibition percentages than the compound 1 on hCA I and hCA II, except compound 14, which is a Mannich base derivative of dipropylamine, which had a similar inhibitory power as compound 1 on hCA II. All compounds synthesized 1-15 were 1.3-1.9 times more effective on hCA II comparing with the effectivenes of the compounds on hCA I.
- Published
- 2016
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10. Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides.
- Author
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Gul HI, Tugrak M, Sakagami H, Taslimi P, Gulcin I, and Supuran CT
- Subjects
- Carbon-13 Magnetic Resonance Spectroscopy, Cell Line, Tumor, Humans, Inhibitory Concentration 50, Proton Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization, Benzenesulfonamides, Sulfonamides chemical synthesis, Sulfonamides pharmacology
- Abstract
A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7-12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1-6) and 4-hydrazinobenzenesulfonamide. The substituted benzaldehydes from which the key intermediate was prepared by introducing 2- or 4-substituents such as fluorine, hydroxy, methoxy, or the 3,4,5-trimethoxy moieties. The compounds were tested for their cytotoxicity, tumor-specificity and potential as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The 3,4,5-trimethoxy and the 4-hydroxy derivatives showed interesting cytotoxic activities, which may be crucial for further anti-tumor activity studies, whereas some of these sulfonamides strongly inhibited both human (h) cytosolic isoforms hCA I and II.
- Published
- 2016
- Full Text
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11. Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities.
- Author
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Tugrak M, Yamali C, Sakagami H, and Gul HI
- Subjects
- Antineoplastic Agents chemical synthesis, Antineoplastic Agents chemistry, Antineoplastic Agents toxicity, Cell Line, Cell Line, Tumor, Cell Survival drug effects, Humans, Hydroxybenzoates chemical synthesis, Hydroxybenzoates chemistry, Hydroxybenzoates toxicity, Indenes chemistry, Mannich Bases chemistry, Molecular Structure, Neoplasms drug therapy, Indenes chemical synthesis, Indenes toxicity, Mannich Bases chemical synthesis, Mannich Bases toxicity
- Abstract
Chalcones and Mannich bases are a group of compounds known for their cytotoxicities. In this study restricted chalcone analogue, compound 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one MT1, was used as a starting compound to synthesize new mono Mannich bases since Mannich bases may induce more cytotoxicity than chalcone analogue that they are derived from by producing additional alkylating center for cellular thiols. In this study, cyclic and acyclic amines were used to synthesize Mannich bases. All compounds were tested against Ca9-22 (gingival carcinoma), HSC-2, HSC-3 and HSC-4 (oral squamous cell carcinoma) as tumour cell lines and HGF (gingival fibroblasts), HPC (pulp cells) and HPLF (periodontal ligament fibroblasts) human normal oral cells as non tumour cell lines. Cytotoxicity, selectivity index (SI) values and potency selectivity expression (PSE) values expressed as a percentage were determined for the compounds. According to data obtained, the compound MT8 with the highest PSE value bearing N-methylpiperazine moiety seems to be a good candidate to develop new cytotoxic compounds and is suited for further investigation.
- Published
- 2016
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12. Synthesis of some acrylophenones with N-methylpiperazine and evaluation of their cytotoxicities.
- Author
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Gul HI, Tugrak M, and Sakagami H
- Subjects
- Antineoplastic Agents chemistry, Cell Line, Cell Proliferation drug effects, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Piperazines chemical synthesis, Piperazines chemistry, Structure-Activity Relationship, Antineoplastic Agents chemical synthesis, Antineoplastic Agents pharmacology, Piperazines pharmacology
- Abstract
In this study, the compounds having acrylophenone structure, 1-aryl-2-(N-methylpiperazinomethyl)-2-propen-1-one dihydrochlorides, were synthesized and their chemical structures were identified with (1)H NMR, (13)C NMR and HRMS spectra. The cytotoxicities of the compounds were tested towards Ca9-22 (human gingival carcinoma), HSC-2 (human oral squamous carcinoma), HSC-3 (human oral squamous carcinoma) and HSC-4 (human oral squamous carcinoma) cell lines as tumor cell lines and HGF (gingival fibroblasts), HPLF (periodontal ligament fibroblasts) and HPC (pulp cells) cell lines as non-tumor cell lines. PSE of the compound TA2, which has a methyl substituent on phenyl ring, pointed out the compound TA2 as a leader compound to be considered.
- Published
- 2016
- Full Text
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13. Radiation Parameters of Some Potential Bioactive Compounds.
- Author
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Gedik Z, Tugrak M, Dastan A, Gul HI, and Yilmaz D
- Subjects
- Molecular Weight, Photons, Antineoplastic Agents chemistry, Mannich Bases
- Abstract
In this study, we aimed to determine the radiation parameters of some potential bioactive compounds. 1-Aryl-3-dibenzylamino-propane-1-on hydrochloride type Mannich bases were synthesized via classical conventional heating method. Aryl part was changed as phenyl (C6H5), 4-methylphenyl (4-CH3C6H4), 4-fluorophenyl ( 4-FC6H4), 4-nitrophenyl (4-NO2C6H4), 4-chlorophenyl (4-ClC6H4), 4-bromophenyl (4-BrC6H4), and 2-thienyl (C4H3S-2-yl). Mass attenuation coefficient (μm), effective atomic number (Z(eff)) and effective electron density (N(el)) of compounds were determined experimentally and theoretically for at 8.040, 8.910, 13.40, 14.96, 17.48, 19.61, 22.16, 24.94, 32.19, 36.38, 44.48, 50.38 and 59.54 keV photon energies by using an HPGe detector with a resolution of 182 eV at 5.9 keV. Radiation parameters of these compounds which can be anti-cancer drug candidate were given in the tables. The results show that phenyl ring behave like thiophene ring in terms of radiation absorption. It is thought that the results of study may drive allow the development of drug candidate new compounds in medical oncology.
- Published
- 2015
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