Design and Synthesis of Novel Imidazo[2,1-b]thiazole Derivatives As Potent Antiviral and Antimycobacterial Agents

Overview

Journal Bioorg Chem

Publisher Elsevier

Specialties Biochemistry
Chemistry

Date 2019 Dec 22

PMID 31862455

Citations 10

Authors

Elif Gursoy

Efe Dogukan Dincel

Lieve Naesens

Nuray Ulusoy Guzeldemirci

Affiliations

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Abstract

A series of novel acyl-hydrazone (4a-d) and spirothiazolidinone (5a-d, 6a-d) derivatives of imidazo[2,1-b]thiazole were synthesized and evaluated for their antiviral and antimycobacterial activity. The antituberculosis activity was evaluated by using the Microplate Alamar Blue Assay and the antiviral activity was evaluated against diverse viruses in mammalian cell cultures. According to the biological activity studies of the compounds, 5a-c displayed hope promising antitubercular activity, 6d was found as potent for Coxsackie B4 virus, 5d was found as effective against Feline corona and Feline herpes viruses. Consequently, the obtained results displayed that, 5a-d and 6d present a leading structure for future drug development due to its straightforward synthesis and relevant bioactivity.

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References

Ulusoy Guzeldemirci N, Kucukbasmaci O . Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur J Med Chem. 2009; 45(1):63-8. DOI: 10.1016/j.ejmech.2009.09.024. View

Vanderlinden E, Goktas F, Cesur Z, Froeyen M, Reed M, Russell C . Novel inhibitors of influenza virus fusion: structure-activity relationship and interaction with the viral hemagglutinin. J Virol. 2010; 84(9):4277-88. PMC: 2863778. DOI: 10.1128/JVI.02325-09. View

Andreani A, Rambaldi M, Locatelli A, Cristoni A, MALANDRINO S, PIFFERI G . Synthesis and antihypertensive activity of imidazo[2,1-b]-thiazoles bearing a 2,6-dichlorophenyl group. Acta Pharm Nord. 1992; 4(2):93-6. View

Parrino B, Carbone A, Ciancimino C, Spano V, Montalbano A, Barraja P . Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: in vitro antiproliferative activity and molecular mechanism(s) of action. Eur J Med Chem. 2015; 94:149-62. DOI: 10.1016/j.ejmech.2015.03.005. View

Janssen P . The levamisole story. Prog Drug Res. 1976; 20:347-83. DOI: 10.1007/978-3-0348-7094-8_11. View

Andreani A, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M . Synthesis and antitubercular activity of imidazo[2,1-b]thiazoles. Eur J Med Chem. 2001; 36(9):743-6. DOI: 10.1016/s0223-5234(01)01266-1. View

Andreani A, Rambaldi M, Leoni A, Locatelli A, Bossa R, Fraccari A . Potential antitumor agents. 24. Synthesis and pharmacological behavior of imidazo[2,1-b]thiazole guanylhydrazones bearing at least one chlorine. J Med Chem. 1996; 39(14):2852-5. DOI: 10.1021/jm9509307. View

Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R . New antitumor imidazo[2,1-b]thiazole guanylhydrazones and analogues. J Med Chem. 2008; 51(4):809-16. DOI: 10.1021/jm701246g. View

Cianci C, Yu K, Dischino D, Harte W, Deshpande M, Luo G . pH-dependent changes in photoaffinity labeling patterns of the H1 influenza virus hemagglutinin by using an inhibitor of viral fusion. J Virol. 1999; 73(3):1785-94. PMC: 104417. DOI: 10.1128/JVI.73.3.1785-1794.1999. View

10.

Angelova V, Karabeliov V, Andreeva-Gateva P, Tchekalarova J . Recent Developments of Hydrazide/Hydrazone Derivatives and Their Analogs as Anticonvulsant Agents in Animal Models. Drug Dev Res. 2016; 77(7):379-392. DOI: 10.1002/ddr.21329. View

11.

Bertamino A, Musella S, Di Sarno V, Ostacolo C, Manfra M, Vanacore D . Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies. Eur J Med Chem. 2015; 102:106-14. DOI: 10.1016/j.ejmech.2015.07.044. View

12.

Andreani A, Rambaldi M, Bonazzi D, Bossa R, Galatulas I . Cardiotonic activity of 2,5-dimethoxyphenylimidazo[2,1-b]thiazoles. Arch Pharm (Weinheim). 1985; 318(11):1003-8. DOI: 10.1002/ardp.19853181109. View

13.

Vintonyak V, Warburg K, Kruse H, Grimme S, Hubel K, Rauh D . Identification of thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase B. Angew Chem Int Ed Engl. 2010; 49(34):5902-5. DOI: 10.1002/anie.201002138. View

14.

Senkardes S, Kaushik-Basu N, Durmaz I, Manvar D, Basu A, Atalay R . Synthesis of novel diflunisal hydrazide-hydrazones as anti-hepatitis C virus agents and hepatocellular carcinoma inhibitors. Eur J Med Chem. 2015; 108:301-308. DOI: 10.1016/j.ejmech.2015.10.041. View

15.

Luo G, Colonno R, Krystal M . Characterization of a hemagglutinin-specific inhibitor of influenza A virus. Virology. 1996; 226(1):66-76. DOI: 10.1006/viro.1996.0628. View

16.

Cascioferro S, Parrino B, Petri G, Cusimano M, Schillaci D, Di Sarno V . 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent staphylococcal biofilm inhibitors. Eur J Med Chem. 2019; 167:200-210. DOI: 10.1016/j.ejmech.2019.02.007. View

17.

Akkurt M, Yalcin S, Ulusoy Guzeldemirci N, Buyukgungor O . N-(3-Oxo-1-thia-4-aza-spiro-[4.5]dec-4-yl)-6-phenyl-imidazo[2,1-b][1,3]thia-zole-3-acetamide hemihydrate. Acta Crystallogr Sect E Struct Rep Online. 2011; 64(Pt 5):o810-1. PMC: 2961240. DOI: 10.1107/S1600536808009306. View

18.

Ulusoy N . Synthesis and antituberculosis activity of cycloalkylidenehydrazide and 4-aza-1-thiaspiro[4.5]decan-3-one derivatives of imidazo[2,1-b]thiazole. Arzneimittelforschung. 2002; 52(7):565-71. DOI: 10.1055/s-0031-1299931. View

19.

Collins L, Franzblau S . Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother. 1997; 41(5):1004-9. PMC: 163841. DOI: 10.1128/AAC.41.5.1004. View

20.

Sun A, Chiang C, Chiou P, Wang J, Liu B, Wu Y . Immunomodulation by levamisole in patients with recurrent aphthous ulcers or oral lichen planus. J Oral Pathol Med. 1994; 23(4):172-7. DOI: 10.1111/j.1600-0714.1994.tb01108.x. View