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Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety

Year 2018, Volume: 22 Issue: 2, 237 - 248, 27.06.2025

Nuray Ulusoy Güzeldemirci , Erkan Pehlivan , Lieve Naesens

Abstract

A series of new 4-thiazolidinone derivatives were synthesized and evaluated against diverse DNA- and RNA-viruses in mammalian cell cultures. Some of the compounds were found to exhibit moderate antiviral activity. 3- Propyl-2-[((6-(4-chlorophenyl)imidazo[2,1-b]thiazol-3-yl)acetyl)hydrazono]-5-methyl-4-thiazolidinone 13, displayed modest yet consistent activity against three strains of influenza A virus, including the 2009 pandemic virus A/H1N1 Virginia/ATCC3/2009 (cytotoxicity >100 µM). Compounds 6 and 11 displayed activity against vesicular stomatitis virus in HeLa cells (antiviral EC50 values of 9 (cytotoxicity 100 µM) and 2 µM (cytotoxicity 20 µM), respectively). Neither of the compounds was active against HIV.

Keywords

antiviral activity imidazo[2,1-b]thiazoles 4-thiazolidines synthesis

References

  • [1] Andreani A, Leoni A, Locatelli A, et al. Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles. Eur J Med Chem. 2013; 68: 412-421.
  • [2] Ali AR, El-Bendary ER, Ghaly MA, Shehata IA. Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b]thiazole derivatives bearing pyrazole moieties. Eur J Med Chem. 2014; 75: 492-500.
  • [3] Budriesi R, Ioan P, Leoni A, et al. Cystic Fibrosis: A new target for 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines. J Med Chem. 2011; 54(11): 3885-3894.
  • [4] Ding H, Chen Z, Zhang C, et al. Synthesis and cytotoxic activity of some novel N-pyridinyl-2-(6-phenylimidazo[2,1-b]thiazol-3-yl)acetamide derivatives. Molecules. 2012; 17(4): 4703-4716.
  • [5] Park J, El-Gamal MI, Lee YS, Oh C. New imidazo[2,1-b]thiazole derivatives: Synthesis, in vitro anticancer evaluation, and in silico studies. Eur J Med Chem. 2011; 46(12): 5769-5777.
  • [6] Fidanze SD, Erickson SA, Wang GT, et al. Imidazo[2,1-b]thiazoles: Multitargeted inhibitors of IGF and EGFR receptor kinases. Bioorg Med Chem. 2010; 20(8): 2452-2455.
  • [7] Juspin T, Laget M, Terme T, et al. TDAE-assisted synthesis of new imidazo[2,1-b]thiazole derivatives as anti-infectious agents. Eur J Med Chem. 2010; 45(2): 840-845.
  • [8] Barradas JS, Errea MI, D’Accorso N, et al. Synthesis and antiviral activity of azoles obtained from carbohydrates. Carbohydr Res. 2008; 343(14): 2468-2474.
  • [9] Mas-Prio J, Torrens-Jover A. Substituted imidazo[2,1-b]thiazole-5-sulfonamide derivatives as 5-HT6 ligands. PCT WO 2009/135925 A1.
  • [10] Aissaoui H, Boss C, Gude M, et al. 3-Aza-bicyclo[3.3.0]octane derivatives as orexin receptor antagonists. PCT WO 2009/004584 A1.
  • [11] Youssef MSK, Ahmed RA, Abbady MS, et al. Synthesis of thiazolo[3,2-α]pyrimidine and imidazo[2,1-b]thiazole derivatives. Monatsh Chem. 2008; 139(5): 553-559.
  • [12] Budriesi R, Ioan P, Locatelli A, et al. Imidazo[2,1-b]thiazole system: A scaffold endowing dihydropyridines with selective cardiodepressant activity. J Med Chem. 2008; 51(6): 1592-1600.
  • [13] Barradas JS, Errea MI, D’Accorso NB, et al. Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus. Eur J Med Chem. 2011; 46(1): 259-264.
  • [14] Harding M, Silas B. Preparation of imidazo[2,1-b][1,3]thiazole-5-carboxamide compounds for HCV treatment. PCT WO 2013075173 A1.
  • [15] Ulusoy N, Çapan G, Ötük G, Kiraz M. Synthesis and antimicrobial activity of new 6-phenylimidazo[2,1-b]thiazole derivatives. Boll Chim Farmaceutico. 2000; 139(4): 167-172.
  • [16] Ulusoy N. Synthesis and antituberculosis activity of cycloalkylidenehydrazide and spiro-thiazolidinone derivatives. Arzneim-Forsch. 2002; 52(7): 565-571.
  • [17] Ulusoy N, Kiraz M, Küçükbasmacı Ö. New 6-(4-Bromophenyl)-imidazo[2,1-b]thiazole derivatives: Synthesis and antimicrobial activity. Monatsh Chem. 2002; 133(10): 1305-1315.
  • [18] Gürsoy E, Ulusoy Güzeldemirci N. Synthesis and cytotoxicity evaluation of new imidazo[2,1-b]thiazole derivatives. Eur J Med Chem. 2007; 42(3): 320-326.
  • [19] Ulusoy Güzeldemirci N, Küçükbasmacı Ö. Synthesis and antimicrobial evaluation of 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole. Eur J Med Chem. 2010; 45(1): 63-68.
  • [20] Ulusoy Güzeldemirci N, Şatana D, Küçükbasmacı Ö. Synthesis and evaluation of new hydrazinecarbothioamide derivatives. J Enzym Inhib Med Chem. 2013; 28(5): 968-973.
  • [21] Masoud GN, Youssef AM, Khalek MMA, et al. Design, synthesis, and biological evaluation of new benzimidazole-substituted 4-thiazolidinones. Med Chem Res. 2013; 22(2): 707-725.
  • [22] Nandagokula C, Poojary B, Vittal S, et al. Synthesis and biological evaluation of N-aryl hydrazones and 4-thiazolidinones. Med Chem Res. 2013; 22(1): 253-266.
  • [23] Sarkanj B, Molnar M, Cacic M, et al. Enhancement of antifungal and antioxidant activity by 4-methyl-7-hydroxycoumarin derivatives. Food Chem. 2013; 139(1): 488-495.
  • [24] Raza S, Srivastava SP, Srivastava DS, et al. Thiazolidin-4-one derivatives as antihyperglycemic and antidyslipidemic agents. Eur J Med Chem. 2013; 63: 611-620.
  • [25] Parmar SS, Dwivedi C, Chaudhari A, Gupta TK. Substituted thiazolidones and inhibition of NAD-dependent oxidations. J Med Chem. 1972; 15(1): 99-101.
  • [26] Joshi P, Anderson C, Binch H, et al. Potent CNS-penetrant thiazolidinones as novel CGRP receptor antagonists. Bioorg Med Chem Lett. 2014; 24(3): 845-849.
  • [27] Bhalgat CM, Darda PV, Bothara KG, et al. Synthesis and pharmacological screening of novel antihypertensive thiazolidinones. Eur J Med Chem. 2014; 76: 580-588.
  • [28] Jain AK, Vaidya A, Ravichandran V, Kashaw SK. Recent developments in thiazolidinone derivatives. Bioorg Med Chem. 2012; 20(11): 3378-3395.
  • [29] Rawal RK, Prabhakar YS, Katti SB, De Clercq E. Selective HIV-RT inhibition by furan-2-ylmethyl-thiazolidin-4-ones. Bioorg Med Chem. 2005; 13(24): 6771-6776.
  • [30] Verma A, Saraf SK. 4-Thiazolidinone: A biologically active scaffold. Eur J Med Chem. 2008; 43(5): 897-905.
  • [31] Küçükgüzel İ, Satılmış G, Gurukumar KR, et al. 2-Heteroarylimino-5-arylidene-4-thiazolidinones as non-nucleoside inhibitors of HCV NS5B polymerase. Eur J Med Chem. 2013; 69: 931-941.
  • [32] Havrylyuk D, Zimenkovsky B, Vasylenko O, et al. Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones. Eur J Med Chem. 2013; 66: 228-237.
  • [33] Barreca ML, Chimirri A, De Luca L, et al. Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents. Bioorg Med Chem Lett. 2001; 11(13): 1793-1796.
  • [34] Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A. 4-Thiazolidinones: The advances continue… Eur J Med Chem. 2014; 72: 52-77.
  • [35] Arnold E, Das K, Ding J, et al. Targeting HIV reverse transcriptase for anti-AIDS drug design. Drug Des Discov. 1996; 13(3-4): 29-47.
  • [36] Gazzard B, Moyle G. 1998 revision to the British HIV Association guidelines for antiretroviral treatment. Lancet. 1998; 352(9124): 314-316.
  • [37] Čačić M, Molnar M, Šarkanj B, et al. Synthesis and antioxidant activity of new coumarinyl-1,3-thiazolidine-4-ones. Molecules. 2010; 15(10): 6795-6809.
  • [38] Özkırımlı S, Kazan F, Tunalı Y. Synthesis, antibacterial and antifungal activities of 3-(1,2,4-triazol-3-il)-4-thiazolidinones. J Enzym Inhib Med Chem. 2009; 24(2): 447-452.
  • [39] Robert JF, Xicluna A, Panouse JJ. Advances in heterocyclic chemistry. Eur J Med Chem Chim Ther. 1975; 10: 59-64.
  • [40] Cesur N, Cesur Z, Güner H, Kasımoğulları Ö. Synthesis of some new imidazothiazoles. Heterocycl Com. 2002; 8(5): 433-438.
  • [41] Kuhmstedt H, Kottke K, Knoke D, et al. Synthesis of amides and heterocyclic acylhydrazides with potential immunomodulator properties. Ann Pharm Fr. 1982; 40: 425-429.
  • [42] Krečmerová M, Holý A, Pohl R, et al. Ester prodrugs of cyclic 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine: Synthesis and antiviral activity. J Med Chem. 2007; 50(23): 5765-5772.
  • [43] Harraga S, Nicod L, Drouhin JP, et al. Imidazo[2,1-b]thiazole derivatives: modulation of CD2-receptor of T lymphocytes. Eur J Med Chem. 1994; 29(4): 309-315.
  • [44] Ulusoy N, Çapan G, Ergenç N, et al. Synthesis and antimicrobial activity of novel imidazo[2,1-b]thiazolylacetylamino/hydrazono 4-thiazolidinones. Acta Pharm Turc. 1997; 39(4): 181-186.
  • [45] Çapan G, Ulusoy N, Ergenç N, et al. Synthesis and antifungal activity of new 6-phenylimidazo[2,1-b]thiazole derivatives. Monatsh Chem. 1999; 130(11): 1399-1407.
  • [46] Vanderlinden E, Göktas F, Cesur Z, et al. Novel inhibitors of Influenza virus fusion: Structure-activity relationship and interaction with viral hemagglutinin. J Virol. 2010; 84(9): 4277–4288.
There are 46 citations in total.

Details

Primary Language English
Subjects Pharmaceutical Chemistry
Journal Section Articles
Authors

Nuray Ulusoy Güzeldemirci 0000-0002-4495-4282

Erkan Pehlivan 0000-0001-9891-3542

Lieve Naesens 0000-0001-9742-9302

Publication Date June 27, 2025
Published in Issue Year 2018 Volume: 22 Issue: 2

Cite

APA Ulusoy Güzeldemirci, N., Pehlivan, E., & Naesens, L. (2025). Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Journal of Research in Pharmacy, 22(2), 237-248.
AMA Ulusoy Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. J. Res. Pharm. June 2025;22(2):237-248.
Chicago Ulusoy Güzeldemirci, Nuray, Erkan Pehlivan, and Lieve Naesens. “Synthesis and Antiviral Activity Evaluation of New 4-Thiazolidinones Bearing an imidazo[2,1-b]thiazole Moiety”. Journal of Research in Pharmacy 22, no. 2 (June 2025): 237-48.
EndNote Ulusoy Güzeldemirci N, Pehlivan E, Naesens L (June 1, 2025) Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Journal of Research in Pharmacy 22 2 237–248.
IEEE N. Ulusoy Güzeldemirci, E. Pehlivan, and L. Naesens, “Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety”, J. Res. Pharm., vol. 22, no. 2, pp. 237–248, 2025.
ISNAD Ulusoy Güzeldemirci, Nuray et al. “Synthesis and Antiviral Activity Evaluation of New 4-Thiazolidinones Bearing an imidazo[2,1-b]thiazole Moiety”. Journal of Research in Pharmacy 22/2 (June 2025), 237-248.
JAMA Ulusoy Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. J. Res. Pharm. 2025;22:237–248.
MLA Ulusoy Güzeldemirci, Nuray et al. “Synthesis and Antiviral Activity Evaluation of New 4-Thiazolidinones Bearing an imidazo[2,1-b]thiazole Moiety”. Journal of Research in Pharmacy, vol. 22, no. 2, 2025, pp. 237-48.
Vancouver Ulusoy Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. J. Res. Pharm. 2025;22(2):237-48.