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1. Synthesis, molecular modeling simulations and anticancer activity of some new Imidazo[2,1-b]thiazole analogues as EGFR/HER2 and DHFR inhibitors.

Author

Moharram, Esraa A., El-Sayed, Selwan M., Ghabbour, Hazem A., and El-Subbagh, Hussein I.

Subjects
*IMIDAZOPYRIDINES, *ANTINEOPLASTIC agents, *THIAZOLES, *CELL cycle, *HELA cells, *CELL lines, *CYTOTOXINS
Abstract

[Display omitted] • Compounds 23 and 39 proved to be the most potent anticancer agents with high SI values. • Compounds 23 and 39 showed their best anticancer potency against MCF-7 breast cell line. • Compounds 23 and 39 proved to be potent EGFR/HER2 inhibitors. • Compounds 23 and 39 induced their cytotoxicity via cell cycle arrest at G0/G1 and G2/M phases, respectively. • Compounds 23 and 39 proved to cause remarkable breast tumor volume reduction. New imidazo[2,1- b ]thiazole analogs were designed, synthesized, and biologically evaluated as anticancer agents. In vitro biological evaluation of the anticancer properties of the compounds was performed against different cancer cell lines. Compounds 23 and 39 showed remarkable broad −spectrum cytotoxic potency on most of the tested cell lines. Compounds 23 and 39 exhibited potent activity against the MCF-7 breast cancer cell line, with IC 50 values of 1.81 and 4.95 μM, respectively, compared to DOX and SOR (IC 50 values of 4.17 and 7.26 μM, respectively). An enzyme inhibition assay was carried out to clarify the possible mode of action of the tested compounds. Compounds 23 and 39 were identified as possible EGFR, HER-2, and DHFR inhibitors. Cell cycle arrest results indicated that compound 23 caused cell cycle arrest at the G0/G1 phase in the MCF-7 cells and at the G2/M phase in the Hep G2 cells. Compound 39 induced cell cycle arrest at the G2/M phase in Hela cells. In vivo testing of the anticancer activity of the two most promising molecules in this study was conducted, and the results indicated that they possess considerable in vivo anticancer activity in mice. Data obtained from the molecular modeling simulation study were consistent with the biological evaluation results. [ABSTRACT FROM AUTHOR]

Published
2024
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2. Colorimetric detection of Pd2+ and Ni2+ ions using a probe having benzo[d]imidazo[2,1-b]thiazole and pyrene rings: Application in detection of Pd2+ ion in anti-hypertensive drugs.

Author

Bhattacharya, Araghni and Manivannan, Vadivelu

Subjects
*PYRENE, *LOSARTAN, *BENZOPYRENE, *BINDING constant, *IONS, *METAL ions, *THIAZOLES
Abstract

[Display omitted] • The sensor, LH , has benzo[ d ]imidazo[2,1- b ]thiazole and pyrene chromophores. • Detection limit of LH is as low as 1.32 ppb (for Pd2+) and 0.54 ppb (for Ni2+). • This probe can detect Pd2+ in the presence of anti-hypertensive drugs. • High binding constant values signified the stable complex formation. • Calculations using Gaussian 16 supported experimentally observed UV–Vis spectra. Pd-complexes are widely used in the pharmaceutical industry to synthesize APIs and drug molecules. It is imperative to detect even trace amounts of Pd impurities in them. A probe (E / Z)- N '-(pyren-1-ylmethylene)benzo[ d ]imidazo[2,1- b ]thiazole-2-carbohydrazide (LH) having benzo[ d ]imidazo[2,1- b ]thiazole and pyrene rings has been synthesized. LH was found to exhibit a change from colourless to yellowish green in presence of Pd2+ and Ni2+ ions. This colorimetric " turn on " response has also been observed with Pd2+ ions in the presence of "sartan" drugs, namely telmisartan, valsartan, irbesartan, olmesartan medoxomil and losartan potassium. The limit of detection ranged from 46.1 to 93.9 nM (4.9 to 6.0 ppb) for PdCl 2 and 10.6 to 19.6 nM (1.1 to 2.1 ppb) for Pd(PPh 3) 2 Cl 2 and these are lower than the limit suggested by the EMA. The LOD values of Ni2+ ion was 9.301 nM which is also lower than the WHO guideline value. This probe showed a remarkable ability to recover Pd2+ ions from the spiked solution of drug samples. The probe formed stable 1:1 complexes with both the metal ions with binding constant values 3.72 × 103 L mol−1 (for Pd2+) and 8.26 × 104 L mol−1 (for Ni2+). Binding constant values of Pd- L complex increased in the presence of drug molecules, thereby indicating the absence of interference. The pH tolerance of the probe was found to be in the range of 3–11 (for Ni2+) and 2–11 (for Pd2+). DFT/TDDFT studies performed on LH , [Pd(L)(CH 3 CN)Cl] and [Ni(LH)(H 2 O)(CH 3 CN)Cl 2 ] in CPCM continuum solvation model in CH 3 CN, showed good correlation between calculated UV–Vis and experimental spectra. [ABSTRACT FROM AUTHOR]

Published
2024
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3. Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase.

Author

Dianat, Shima, Moghimi, Setareh, Mahdavi, Mohammad, Nadri, Hamid, Moradi, Alireza, Firoozpour, Loghman, Emami, Saeed, Mouradzadegun, Arash, Shafiee, Abbas, and Foroumadi, Alireza

Subjects
*ENZYME inhibitors, *LIPOXYGENASES, *HETEROCYCLIC compounds, *QUINOLINE, *IMIDAZOLES, *SOYBEAN
Abstract

A series of 2-chloro-quinoline-based imidazopyridines 6a-l and imidazothiazoles 6m-o bearing a bulky alkylamine side chain were synthesized as soybean 15-LOX inhibitors. The target compounds 6a-o were prepared via one-pot reaction of 2-chloroquinoline-3-carbaldehyde (3), heteroaromatic amidine 4, and alkyl isocyanides 5, in the presence of NH4Cl. All compounds showed significant anti-15-LOX activity (IC50 values≤40 μM). Among the title compounds, the imidazo[2,1-b]thiazole derivative 6n bearing a tert-butylamine moiety showed the highest activity against soybean 15-LOX enzyme. [ABSTRACT FROM AUTHOR]

Published
2016
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4. Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety

Author

Selin Cimok, Net Das-Evcimen, Mutlu Sarikaya, and Nuray Ulusoy Güzeldemirci

Subjects
chemistry.chemical_classification, Aldose reductase, Aldose reductase inhibition, Chemistry, Stereochemistry, Hydrazinecarbothioamide, lcsh:RS1-441, Pharmaceutical Science, Rat kidney, imidazo[2, lcsh:Pharmacy and materia medica, chemistry.chemical_compound, 1-b]thiazole, 4-thiazolidinone, Molecular Medicine, Moiety, Thiazole, Inhibitory effect, Alkyl
Abstract

Objectives To synthesize and characterize 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamide and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinone derivatives and evaluate them for their aldose reductase (AR) inhibitory effect. Materials and methods 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamides (3a-f) and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinones (4a-j) were synthesized from 2-[6-(4-bromophenyl)imidazo[2,1-b]thiazole-3-yl]acetohydrazide (2). Their structures were elucidated by elemental analyses and spectroscopic data. The synthesized compounds were tested for their ability to inhibit rat kidney AR. Results Among the synthesized compounds, 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-benzoylhydrazinecarbothioamide (3d) showed the best AR inhibitory activity. Conclusion The findings of this study indicate that the different derivatives of the compounds in this study may be considered interesting candidates for future research.

Published
2019

5. Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems

Author

Maruyama, Takahisa, Kano, Yuko, Yamamoto, Yasuo, Kurazono, Mizuyo, Iwamatsu, Katsuyoshi, Atsumi, Kunio, and Shitara, Eiki

Subjects
*STAPHYLOCOCCUS aureus, *METHICILLIN resistance, *ANTIBACTERIAL agents, *HAEMOPHILUS influenzae
Abstract

Abstract: A new series of 1β-methyl carbapenems, possessing a 7-substituted imidazo[5,1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus, was synthesized and evaluated for antibacterial activity. These compounds showed potent activities against Gram-positive bacteria, in particular methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae (PRSP). They also exhibited potent activity against β-lactamase-negative ampicillin-resistant Haemophilus influenzae (BLNAR). [Copyright &y& Elsevier]

Published
2007
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6. Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1-b]thiazole Moiety

Author

Nuray ULUSOY GÜZELDEMİRCİ, Berin KARAMAN, and Ömer KÜÇÜKBASMACI

Subjects
lcsh:Pharmacy and materia medica, antibacterial activity, 1-b]thiazole, antiviral activity, arylidenehydrazide, lcsh:RS1-441, antitubercular activity, Imidazo[2
Abstract

Objectives: The aim of this study was to determine the probable antibacterial, antitubercular, and antiviral activities of some N2-arylidene-(6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl) acetic acid hydrazides (3a-j). Further structural optimization of the identified lead structures can lead us to new more active potential antibacterial, antitubercular, and antiviral agents. Materials and Methods: Antibacterial activities of the title compounds against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853 and Escherichia coli ATCC 25922. These molecules were also evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the BACTEC 460 radiometric system and BACTEC 12B medium. Moreover, all the compounds (3a-j) were also evaluated against some DNA and RNA viruses in Madin-Darby Canine Kidney, Crandell-Rees Feline Kidney (CRFK), Vero, human embryonic lung (HEL) and HeLa cells. Results: Among the tested compounds, 3i displayed the highest efficacy against S. aureus and E. coli. Compound 3j, 5-nitro-2-furfurylidene derivative showed the highest antituberculosis activity (IC50: 6.16 µg/mL and IC90: 14.390 µg/mL). Compound 3i showed the most potent antiviral activity against feline corona virus in CRFK cell cultures (antiviral EC50: 7.5 µM and SI>13). Furthermore, compounds 3c and 3g displayed activity against herpes simplex virus-1 and vaccinia virus in HEL cell cultures (antiviral EC50 values of 9; 16 and 20; 14 µM, respectively). Conclusion: On the basis of aforementioned results, it can be conluded that imidazo[2,1-b]thiazole derivatives bearing hydrazone moieties serve as promising chemical probes to design therapeutic agents with antibacterial, antitubercular, and antiviral properties.

Published
2017

7. New 6-(4-Bromophenyl)-imidazo[2,1- b]thiazole Derivatives: Synthesis and Antimicrobial Activity.

Author

Ulusoy, Nuray, Kiraz, Muammer, and Küçükbasmacı, Ömer

Abstract

New 4-alkyl/aryl-1-((6-(4-bromophenyl)-imidazo[2,1- b]thiazol-3-yl)-acetyl)-3-thiosemicarbazides and 3-alkyl/aryl-2-(((6-(4-bromophenyl)-imidazo[2,1- b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinones were synthesized from 6-(4-bromophenyl)-imidazo[2,1- b]thiazole-3-acetic acid hydrazide. Their structures were elucidated by elemental analyses and spectroscopic data. All compounds were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by the microbroth dilution technique. The compounds were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294); they exhibited varying degrees of inhibition in the in vitro primary screening at 6.25 μg · cm−3. The most active compound was 3-(4-nitrophenyl)-2-(((6-(4-bromophenyl)-imidazo[2,1- b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinone. [ABSTRACT FROM AUTHOR]

Published
2002
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8. Synthesis of 3-(Imidazo[2,1-b]thiazol-6-yl)-2H-chromen-2-one derivatives and study of their antiviral activity against parvovirus B19

Author

Ilaria Conti, Alberto Leoni, Giorgio Gallinella, Gloria Bua, Alessandra Locatelli, Mirella Rambaldi, Rita Morigi, Conti, Ilaria, Morigi, Rita, Locatelli, Alessandra, Rambaldi, Mirella, Bua, Gloria, Gallinella, Giorgio, and Leoni, Alberto

Subjects
viruses, Pharmaceutical Science, Parvovirus B19, Pharmacology, Virus Replication, Analytical Chemistry, Coumarins, Drug Discovery, Parvovirus B19, Human, Antiviral activity, Cells, Cultured, Imidazo[2, 0303 health sciences, Molecular Structure, biology, Chemistry, virus diseases, Biological activity, Chemistry (miscellaneous), Molecular Medicine, Chromen-2-one, Cell Survival, Coumarin, Antiviral Agents, Article, Virus, NO, Parvoviridae Infections, lcsh:QD241-441, Structure-Activity Relationship, 03 medical and health sciences, lcsh:Organic chemistry, 1-b]thiazole, Humans, Benzopyrans, Viability assay, Physical and Theoretical Chemistry, Cell Proliferation, 030304 developmental biology, 030306 microbiology, Parvovirus, Drug Discovery3003 Pharmaceutical Science, Organic Chemistry, Imidazo[2,1-b]thiazole, imidazo[2,1-b]thiazole, biology.organism_classification, Molecular medicine, Viral replication, Cell culture, 3003
Abstract

Parvovirus B19 (B19V) is a human pathogenic virus associated with a wide range of clinical conditions. Currently, there are no recognized antiviral drugs for B19V treatment, therefore, efforts in the search for compounds inhibiting B19V replication are now being pursued. Coumarins (chromen-2-ones) are considered a privileged structure for designing novel orally bioavailable and non-peptidic antiviral agents. To further contribute to the development of new drugs against B19V, our research was focused on the synthesis, characterization and evaluation of antiviral activity of some new 3-(imidazo[2,1-b]thiazol-6-yl)-2H-chromen-2-one derivatives. The effects of the synthesized compounds on cell viability and viral replication were investigated by employing two relevant cellular systems, the myeloblastoid cell line UT7/EpoS1 and primary erythroid progenitor cells (EPCs). Some of the tested compounds showed inhibitory activity both on cell viability and on viral replication, depending on the cellular system. These results suggest that the mechanism involved in biological activity is sensitive to small structural changes and that it is possible to direct the activity of the 3-(imidazo[2,1-b]thiazol-6-yl)-2H-chromen-2-one core.

Published
2019

9. Design, Synthesis and Biological Evaluation of New Imidazo[2,1-b]Thiazole Derivatives as Selective COX-2 Inhibitors

Author

Shahrasbi, Mahsa, Azami Movahed, Mahsa, Ghorban Dadras, Orkideh, Daraei, Bahram, and Zarghi, Afshin

Subjects
Synthesis, Design, Molecular modeling, Original Article, Cyclooxygenase-2 inhibition, 1-b]Thiazole, Imidazo[2
Abstract

A new series of imidazo[2,1-b]thiazole analogs containing a methyl sulfonyl COX-2 pharmacophore was synthesized and evaluated for their COX-2 inhibitory activity. According to in-vitro COX-1/COX-2 inhibition data, all compounds (6a-g) were selective inhibitors of COX-2 isoenzyme with IC50 values in the highly potent 0.08-0.16 µM range. These results indicated that both potency and selectivity of COX-2 inhibitory activity were affected by the type and size of amine on C-5 of imidazo[2,1-b]thiazole ring. Our data identified N,N-dimethyl-1-(6-(4-(methylsulfonyl)phenyl)imidazo[2,1-b]thiazol-5-yl)methanamine (6a) as a potent and selective COX-2 inhibitor (IC50 COX-1 >100 µM; IC50 COX-2 = 0.08 µM; selectivity index = 313.7). Our results indicated that both potency and selectivity of COX-2 inhibitory activity were affected by the type and size of amine on C-5 of imidazo[2,1-b]thiazole ring.

Published
2018

11. Investigation on the Effects of Antimicrobial imidazo[2,1-b]thiazole Derivatives on the Genitourinary Microflora

Author

Cecilia Prata, Alessandra Locatelli, Rogers Alberto Nahui Palomino, Rita Morigi, Mirella Rambaldi, Beatrice Vitali, Alessandra Graziadio, Alberto Leoni, Morigi, Rita, Vitali, Beatrice, Prata, Cecilia, Palomino, Rogers A. A, Graziadio, Alessandra, Locatelli, Alessandra, Rambaldi, Mirella, and Leoni, Alberto

Subjects
1‐b]thiazole, lactobacilli, 0301 basic medicine, Antifungal Agents, Stereochemistry, Thiazolidine, Urogenital System, bifidobacteria, Antineoplastic Agents, antiproliferative effects, 02 engineering and technology, Microbial Sensitivity Tests, 03 medical and health sciences, chemistry.chemical_compound, Ampicillin, Lactobacillus, Drug Discovery, medicine, Humans, Thiazole, Imidazo[2, urogenital pathogens, biology, Chemistry, Imidazoles, 021001 nanoscience & nanotechnology, Antimicrobial, biology.organism_classification, Anti-Bacterial Agents, Thiazoles, 030104 developmental biology, Nitrogen atom, Bifidobacterium, Econazole, 0210 nano-technology, Imidazothiazole derivatives, Bacteria, medicine.drug, HeLa Cells
Abstract

Background Fused five-membered heterocyclic rings containing bridgehead nitrogen atom are particularly versatile in the field of medicinal chemistry because of their different biological activities. Among them, the imidazo[2,1-b]thiazole is an attractive fused heterocyclic core that has been extensively studied. Objective The aim of the current study was to study the therapeutic applications of imidazo[2,1- b]thiazole derivatives as antimicrobial agents for the treatment of genitourinary infections. Method A traditional synthetic methodology was involved to obtain a small series of imidazothiazole derivatives. Results Herein, we report the antimicrobial activity of the imidazo[2,1-b]thiazole or imidazo[2,1- b]thiazolidine derivatives against selected fungi, Gram-positive and Gram-negative bacteria. Moreover, experiments were carried out to investigate the interference towards the endogenous microbiota. Conclusion The most interesting of the series are the thiocyano derivatives (19, 23) showing a good profile for the treatment of genitourinary infections: a spectrum of activity covering both bacteria and fungi together with a reduced impact versus critical lines of Lactobacillus exerting defense against pathogens.

Published
2017

12. Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1

Author

Nuray, Ulusoy Güzeldemirci, Selin, Cimok, Net, Daş-Evcimen, and Mutlu, Sarikaya

Subjects
Aldose reductase inhibition, Hydrazinecarbothioamide, 1-b]thiazole, Original Article, 4-thiazolidinone, imidazo[2
Abstract

Objectives: To synthesize and characterize 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamide and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinone derivatives and evaluate them for their aldose reductase (AR) inhibitory effect. Materials and Methods: 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-alkyl/arylhydrazinecarbothioamides (3a-f) and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinones (4a-j) were synthesized from 2-[6-(4-bromophenyl)imidazo[2,1-b]thiazole-3-yl]acetohydrazide (2). Their structures were elucidated by elemental analyses and spectroscopic data. The synthesized compounds were tested for their ability to inhibit rat kidney AR. Results: Among the synthesized compounds, 2-[[6-(4-bromophenyl)imidazo[2,1-b]thiazol-3-yl]acetyl]-N-benzoylhydrazinecarbothioamide (3d) showed the best AR inhibitory activity. Conclusion: The findings of this study indicate that the different derivatives of the compounds in this study may be considered interesting candidates for future research.

Published
2017

13. Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1

Author

Nuray, Ulusoy Güzeldemirci, Berin, Karaman, and Ömer, Küçükbasmaci

Subjects
antibacterial activity, 1-b]thiazole, antiviral activity, arylidenehydrazide, Original Article, antitubercular activity, Imidazo[2
Abstract

Objectives: The aim of this study was to determine the probable antibacterial, antitubercular, and antiviral activities of some N2-arylidene-(6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl) acetic acid hydrazides (3a-j). Further structural optimization of the identified lead structures can lead us to new more active potential antibacterial, antitubercular, and antiviral agents. Materials and Methods: Antibacterial activities of the title compounds against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853 and Escherichia coli ATCC 25922. These molecules were also evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the BACTEC 460 radiometric system and BACTEC 12B medium. Moreover, all the compounds (3a-j) were also evaluated against some DNA and RNA viruses in Madin-Darby Canine Kidney, Crandell-Rees Feline Kidney (CRFK), Vero, human embryonic lung (HEL) and HeLa cells. Results: Among the tested compounds, 3i displayed the highest efficacy against S. aureus and E. coli. Compound 3j, 5-nitro-2-furfurylidene derivative showed the highest antituberculosis activity (IC50: 6.16 µg/mL and IC90: 14.390 µg/mL). Compound 3i showed the most potent antiviral activity against feline corona virus in CRFK cell cultures (antiviral EC50: 7.5 µM and SI>13). Furthermore, compounds 3c and 3g displayed activity against herpes simplex virus-1 and vaccinia virus in HEL cell cultures (antiviral EC50 values of 9; 16 and 20; 14 µM, respectively). Conclusion: On the basis of aforementioned results, it can be conluded that imidazo[2,1-b]thiazole derivatives bearing hydrazone moieties serve as promising chemical probes to design therapeutic agents with antibacterial, antitubercular, and antiviral properties.

Published
2016

14. Chemiluminescent high-throughput microassay applied to imidazo[2,1-b]thiazole derivatives as potential acetylcholinesterase and butyrylcholinesterase inhibitors

Author

Aldo Andreani, Massimiliano Granaiola, Silvia Burnelli, Rita Morigi, Alessandra Locatelli, Massimo Guardigli, Aldo Roda, Alberto Leoni, Mirella Rambaldi, M. Rizzoli, Lucilla Varoli, A. Andreani, S. Burnelli, M. Granaiola, M. Guardigli, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, M. Rizzoli, L. Varoli, and A. Roda

Subjects
Alkylation, ANTIBUTYRYLCHOLINESTERASE ACTIVITY, Acylation, IMIDAZO[2, Chemical synthesis, Inhibitory Concentration 50, chemistry.chemical_compound, Drug Discovery, Animals, Thiazole, Butyrylcholinesterase, Cholinesterase, Pharmacology, chemistry.chemical_classification, Binding Sites, Dose-Response Relationship, Drug, biology, Organic Chemistry, Imidazoles, Benzene, Biological activity, General Medicine, Acetylcholinesterase, CHEMILUMINESCENCE, Kinetics, Thiazoles, Enzyme, ANTIACETYLCHOLINESTERASE ACTIVITY, chemistry, Biochemistry, Enzyme inhibitor, Drug Design, Luminescent Measurements, biology.protein, Cholinesterase Inhibitors, 1-B]THIAZOLE
Abstract

The synthesis of a new series of imidazo[2,1-b]thiazole derivatives is described. They were tested as potential acetylcholinesterase and butyrylcholinesterase inhibitors by means of a chemiluminescent microassay. Although most of the new compounds did not show significant cholinesterase inhibition potency, three of them displayed selective antiacetylcholinesterase activity in the micromolar range.

Published
2008

15. Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1- b ]Thiazole Moiety.

Author

Ulusoy Güzeldemirci N, Cimok S, Daş-Evcimen N, and Sarikaya M

Abstract

Objectives: To synthesize and characterize 2-[[6-(4-bromophenyl)imidazo[2,1- b ]thiazol-3-yl]acetyl]- N -alkyl/arylhydrazinecarbothioamide and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1- b ]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinone derivatives and evaluate them for their aldose reductase (AR) inhibitory effect., Materials and Methods: 2-[[6-(4-bromophenyl)imidazo[2,1- b ]thiazol-3-yl]acetyl]- N -alkyl/arylhydrazinecarbothioamides ( 3a-f ) and 3-alkyl/aryl-2-[((6-(4-bromophenyl)imidazo[2,1- b ]thiazol-3-yl)acetyl)hydrazono]-5-nonsubstituted/methyl-4-thiazolidinones ( 4a-j ) were synthesized from 2-[6-(4-bromophenyl)imidazo[2,1- b ]thiazole-3-yl]acetohydrazide ( 2 ). Their structures were elucidated by elemental analyses and spectroscopic data. The synthesized compounds were tested for their ability to inhibit rat kidney AR., Results: Among the synthesized compounds, 2-[[6-(4-bromophenyl)imidazo[2,1- b ]thiazol-3-yl]acetyl]- N -benzoylhydrazinecarbothioamide ( 3d ) showed the best AR inhibitory activity., Conclusion: The findings of this study indicate that the different derivatives of the compounds in this study may be considered interesting candidates for future research., Competing Interests: Conflict of Interest: No conflict of interest was declared by the authors., (©Copyright 2019 Turk J Pharm Sci, Published by Galenos Publishing House.)

Published
2019
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16. Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles

Author

Emanuela Greco, Eun-Jung Park, Aldo Andreani, Ke Huang, Alessandra Locatelli, Richard B. van Breemen, Rinaldo Cervellati, Alberto Leoni, Tamara P. Kondratyuk, Mirella Rambaldi, John M. Pezzuto, Rita Morigi, Aldo Andreani, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella Rambaldi, Rinaldo Cervellati, Emanuela Greco, Tamara P. Kondratyuk, Eun-Jung Park, Ke Huang, Richard B. van Breemen, and John M. Pezzuto

Subjects
Antioxidant, Cell Survival, medicine.medical_treatment, Nitric Oxide Synthase Type II, Antioxidants, Cell Line, chemistry.chemical_compound, Inhibitory Concentration 50, Chemopreventive agent, POLYPHENOLS, Drug Discovery, medicine, 1-b]thiazole, Animals, Anticarcinogenic Agents, Humans, Aromatase, No production, Bifunctional, Cells, Cultured, Imidazo[2, Pharmacology, biology, Human liver, Molecular Structure, Aromatase Inhibitors, Organic Chemistry, Imidazoles, NF-kappa B, Biological activity, General Medicine, Azepines, Hydrogen-Ion Concentration, Thiazoles, Biochemistry, chemistry, COS Cells, biology.protein, Microsome, Microsomes, Liver, Tumor necrosis factor alpha
Abstract

The synthesis of new imidazo[2,1-b]thiazoles bearing phenolic groups is reported. These compounds and some previously described analogs were evaluated as antioxidant agents with three chemical model systems, and cancer chemopreventive potential was examined by inhibition of NO production, TNF-a activated NFkB activity, and aromatase activity, as well as induction of QR1 and RXRE binding. Two of the test compounds, 9 and 12, displayed promising activity by inhibiting iNOS, NFkB and aromatase in dose edependent manner, with IC50 values in low micromolar range. The same compounds activated QR1 in a bifunctional manner. When incubated with human liver microsomes, the active compounds were further hydroxylated on the parent ring system, suggesting the next logical step in the development of these promising leads will entail synthetic production of metabolites followed by additional assessment of biological activity.

Published
2013

17. Synthesis and Chemiluminescent High Throughput Screening for Inhibition of Acetylcholinesterase Activity by Imidazo[2,1-b]thiazole Derivatives

Author

Massimo Guardigli, Aldo Roda, Aldo Andreani, Alberto Leoni, Massimiliano Granaiola, Alessandra Locatelli, Mirella Rambaldi, Rita Morigi, ALDO ANDREANI, MASSIMILIANO GRANAIOLA, MASSIMO GUARDIGLI, ALBERTO LEONI, ALESSANDRA LOCATELLI, RITA MORIGI, MIRELLA RAMBALDI, and ALDO RODA

Subjects
medicine.drug_class, IMIDAZO[2, High-throughput screening, Neuromuscular transmission, Drug Evaluation, Preclinical, Carboxamide, Chemical synthesis, Sensitivity and Specificity, law.invention, Structure-Activity Relationship, chemistry.chemical_compound, law, Drug Discovery, medicine, Organic chemistry, Thiazole, Chemiluminescence, Pharmacology, biology, Bicyclic molecule, Molecular Structure, ALZHEIMERE'S DISEASE, Organic Chemistry, Imidazoles, General Medicine, Combinatorial chemistry, Acetylcholinesterase, BISAMMONIUM SALT, Thiazoles, Inhibitory potency, ANTIACETYLCHOLINESTERASE ACTIVITY, chemistry, Enzyme inhibitor, CHEMILUMINESCENT, Luminescent Measurements, biology.protein, 1-B]THIAZOLE
Abstract

The synthesis of a new series of imidazo[2,1-b]thiazole derivatives is described. They were tested as acetylcholinesterase inhibitors by means of a chemiluminescent method suitable for high throughput screening. The compounds without quaternization had no appreciable inhibitory potency probably because they are poorly soluble in water. The corresponding quaternized compounds were good inhibitors with activity related to the spacer employed.

Published
2006

18. Potential antitumor agents. 34.(1) Synthesis and antitumor activity of guanylhydrazones from imidazo[2,1-b]thiazoles and from diimidazo[1,2-a: 1,2-c] pyrimidine

Author

Andreani, A., Granaiola, M., ALBERTO LEONI, Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Garaliene, V., ANDREANI A., GRANAIOLA M., LEONI A., LOCATELLI A., MORIGI R., RAMBALDI M., GIORGI G., and GARALIENE V.

Subjects
Molecular Structure, IMIDAZO[2, Hydrazones, Imidazoles, Antineoplastic Agents, DIIMIDAZO[1, Crystallography, X-Ray, Guanidines, ANTITUMOR ACTIVITY, 2-A:1, Thiazoles, GUANYLHYDRAZONES, Pyrimidines, Cell Line, Tumor, Humans, 2-C]PYRIMIDINE, Drug Screening Assays, Antitumor, 1-B]THIAZOLE
Abstract

We report the synthesis of new guanylhydrazones from imidazo[2,1-b]thiazoles and of a bis-guanylhydrazone from diimidazo[1,2-a:1,2-c]pyrimidine. The compounds were tested as potential antitumor agents at the National Cancer Institute. Two derivatives are now under review by BEC: one of these was also subjected to a test for positive inotropic activity in view of a possible coanthracyclinic activity. Tyrosine kinase receptors may be involved as molecular targets in the mechanism of action of the guanylhydrazones described.

Published
2004

19. Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1- b ]thiazole Moiety.

Author

Ulusoy Güzeldemirci N, Karaman B, and Küçükbasmaci Ö

Abstract

Objectives: The aim of this study was to determine the probable antibacterial, antitubercular, and antiviral activities of some N 2 -arylidene-(6-(4-chlorophenyl)imidazo[2,1- b ]thiazol-3-yl) acetic acid hydrazides (3a-j) . Further structural optimization of the identified lead structures can lead us to new more active potential antibacterial, antitubercular, and antiviral agents., Materials and Methods: Antibacterial activities of the title compounds against Staphylococcus aureus ATCC 29213, Pseudomonas aeruginosa ATCC 27853 and Escherichia coli ATCC 25922. These molecules were also evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the BACTEC 460 radiometric system and BACTEC 12B medium. Moreover, all the compounds (3a-j) were also evaluated against some DNA and RNA viruses in Madin-Darby Canine Kidney, Crandell-Rees Feline Kidney (CRFK), Vero, human embryonic lung (HEL) and HeLa cells., Results: Among the tested compounds, 3i displayed the highest efficacy against S. aureus and E. coli . Compound 3j , 5-nitro-2-furfurylidene derivative showed the highest antituberculosis activity (IC 50 : 6.16 µg/mL and IC 90 : 14.390 µg/mL). Compound 3i showed the most potent antiviral activity against feline corona virus in CRFK cell cultures (antiviral EC 50 : 7.5 µM and SI>13). Furthermore, compounds 3c and 3g displayed activity against herpes simplex virus-1 and vaccinia virus in HEL cell cultures (antiviral EC 50 values of 9; 16 and 20; 14 µM, respectively)., Conclusion: On the basis of aforementioned results, it can be conluded that imidazo[2,1- b ]thiazole derivatives bearing hydrazone moieties serve as promising chemical probes to design therapeutic agents with antibacterial, antitubercular, and antiviral properties., Competing Interests: Conflict of Interest: No conflict of interest was declared by the authors., (©Copyright 2017 Turk J Pharm Sci, Published by Galenos Publishing House.)

Published
2017
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20. 1H nuclear magnetic resonance spectra of the imidazo[2,1-b]thiazole system

Author

Leonardo Marchetti, Luciano Pentimalli, Ferdinando Taddei, Paolo Lazzeretti, and Luisa Schenetti

Subjects
Coupling constant, chemistry.chemical_compound, Nuclear magnetic resonance, Chemistry, Chemical shift, Electromagnetic shielding, 1-b]thiazole, 1H nuclear magnetic resonance spectra, imidazo[2, Thiazole, Spectral line, Ring current
Abstract

Some imidazo[2,1-b]thiazoles have been subjected to a 1H n.m.r. investigation. The aromatic character of this ring system, in connection with proton shielding, has been tested with coupled Hartree–Fock calculations of ring current effects, and it seems that the main differences in the chemical shifts relative to the single ring heterocycles are due to this kind of perturbation. A long-range coupling constant over six bonds has also been observed which implies a coupling mechanism involving the sulphur atom.

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