Yıl: 2018 Cilt: 22 Sayı: 2 Sayfa Aralığı: 237 - 248 Metin Dili: İngilizce DOI: 10.12991/mpj.2018.61 İndeks Tarihi: 27-02-2020

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

Öz:
A series of new 4-thiazolidinone derivatives were synthesized and evaluated against diverse DNA- andRNA-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, displayedmodest yet consistent activity against three strains of influenza A virus, including the 2009 pandemic virus A/H1N1Virginia/ATCC3/2009 (cytotoxicity >100 μM). Compounds 6 and 11 displayed activity against vesicular stomatitisvirus in HeLa cells (antiviral EC50 values of 9 (cytotoxicity 100 μM) and 2 μM (cytotoxicity 20 μM), respectively). Neitherof the compounds was active against HIV.
Anahtar Kelime:

Konular: Farmakoloji ve Eczacılık
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • [1] Andreani A, Leoni A, Locatelli A, Morigi R, Rambaldi M, Cervellati R, Greco E, Kondratyuk TP, Park EJ, Huang K, Van Breemen RB, Pezzuto JM. 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, Pedemonte N, Locatelli A, Micucci M, Chiarini A, Galietta LJV. 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, Xin T, Wang Y, Song H, Jiang Y, Chen Y, Xu Y, Tan C. 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, Mantei R, Clark RF, Sorensen BK, Bamaung NY, Kovar P, Johnson EF, Swinger KK, Stewart KD, Zhang Q, Tucker LA, Pappano WN, Wilsbacher JL, Wang J, Sheppard GS, Bell RL, Davidsen SK, Hubbard RD. Imidazo[2,1- b]thiazoles: Multitargeted inhibitors of both the insulin-like growth factor receptor and members of the epidermal growth factor family of receptor tyrosine kinases. Bioorg Med Chem. 2010; 20(8): 2452- 2455.
  • [7] Juspin T, Laget M, Terme T, Azas N, Vanelle P. 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, Sepúlveda CS, Talarico LB, Damonte EB. Synthesis and antiviral activity of azoles obtained from carbohydrates. Carbohydr Res. 2008; 343(14): 2468-2474.
  • [9] Mas-Prió J, Torrens-Jover A. Substituted imidazo[2,1-b]thiazole-5-sulfonamide derivatives as 5-HT6 ligands. PCT, World Intellectual Property Organization. 2009; WO 2009/135925 A1.
  • [10] Aissaoui H, Boss C, Gude M, Koberstein R, Sifferlen T. 3-Aza-bicyclo[3.3.0]octane derivatives as orexin receptors antagonists and their preparation, pharmaceutical compositions and use in the treatment of diseases. PCT, World Intellectual Property Organization. 2009; WO 2009/004584 A1.
  • [11] Youssef MSK, Ahmed RA, Abbady MS, Abdel-Mohsen SA, Omar AA. Reactions of 4-(2-aminothiazole-4-yl)-3- methyl-5-oxo-1-phenyl-2-pyrazoline. 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, Cosconati S, Leoni A, Ugenti MP, Andreani A, Di Toro R, Bedini A, Spampinato S, Marinelli L, Novellino E, Chiarini A. 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, Sepúlveda CS, Damonte EB. Imidazo[2,1- b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever. 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 the treatment of HCV. From PCT Int. Appl. 2013; WO 2013075173 A1 20130530.
  • [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 4- aza-1-thiaspiro[4.5]decan-3- one derivatives of imidazo[2,1-b]thiazole. Arzneim-Forsch/Drug Res. 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 primary 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 activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur J Med Chem. 2010; 45(1): 63-68.
  • [20] Ulusoy Güzeldemirci N, Şatana D, Küçükbasmacı Ö. Synthesis, characterization, and antimicrobial evaluation of some new hydrazinecarbothioamide, 1,2,4-triazole and 1,3,4-thiadiazole derivatives. J Enzym Inhib Med Chem. 2013; 28(5): 968-973.
  • [21] Masoud GN, Youssef AM, Khalek MMA, Wahab AEA, Labouta IM, Hazzaa AAB. Design, synthesis, and biological evaluation of new 4-thiazolidinone derivatives substituted with benzimidazole ring as potential chemotherapeutic agents. Med Chem Res. 2013; 22(2): 707-725.
  • [22] Nandagokula C, Poojary B, Vittal S, Shenoy S, Shetty P, Tangavelu A. Synthesis, characterization, and biological evaluation of some N-aryl hydrazones and their 2,3-disubstituted-4-thiazolidinone derivatives. Med Chem Res. 2013; 22(1): 253-266.
  • [23] Sarkanj B, Molnar M, Cacic M, Gille L. 4-Methyl-7-hydroxycoumarinantifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties. Food Chem. 2013; 139(1): 488-495.
  • [24] Raza S, Srivastava SP, Srivastava DS, Srivastava AK, Haq W, Katti SB. Thiazolidin-4-one and thiazinan-4-one derivatives analogous to rosiglitazone as potential antihyperglycemic and antidyslipidemic agents. Eur J Med Chem. 2013; 63: 611-620.
  • [25] Parmar SS, Dwivedi C, Chaudhari A, Gupta TK. Substituted thiazolidones and their selective inhibition of nicotinamide-adenin dinucleotide depented oxidations. J Med Chem. 1972; 15(1): 99-101.
  • [26] Joshi P, Anderson C, Binch H, Hadida S, Yoo S, Bergeron D, Decker C, Terhaar E, Moore J, Garcia-Guzman M, Termin A. Identification of 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, Bhandari SV, Gandhi J, Ramesh B. Synthesis and pharmacological screening of some novel antihypertensive agents possessing 5-benzylidene-2-(phenylimino)-thiazolidin-4-one ring. Eur J Med Chem. 2014; 76: 580-588.
  • [28] Jain AK, Vaidya A, Ravichandran V, Kashaw SK. Recent developments and biological activities of thiazolidinone derivatives: A review. Bioorg Med Chem. 2012; 20(11): 3378-3395.
  • [29] Rawal RK, Prabhakar YS, Katti SB, De Clercq E. 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as selective HIV-RT inhibitors. 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, Basu A, Tatar E, Nichols DB, Talele TT, Kaushik-Basu N. 2- Heteroarylimino-5-arylidene-4-thiazolidinones as a new class of non-nucleoside inhibitors of HCV NS5B polymerase. Eur J Med Chem. 2013; 69: 931-941.
  • [32] Havrylyuk D, Zimenkovsky B, Vasylenko O, Day CW, Smee DF, Grellier P, Lesyk R. Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones. Eur J Med Chem. 2013; 66: 228-237.
  • [33] Barreca ML, Chimirri A, Luca LDe, Monforte AM, Monforte P, Rao A, Zappala M, Balzarini J, Clercq Ede, Pannecouque C, Witvrouw M. 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, Yadav PN, Hsiou Y, Boyer PI, Hughes SH. Targeting HIV reverse transcriptase for anti- AIDS drug design: Structural and biological considerations for chemotherapeutic strategies. Drug Des Discov. 1996; 13(3-4): 29-47.
  • [36] Gazzard B, Moyle G. and on behalf of the BHIVA Guidelines Writing Committee. 1998 revision to the British HIV Association guidelines for antiretroviral treatment of HIV seropositive individuals. Lancet 1998; 352(9124): 314-316.
  • [37] Čačić M, Molnar M, Šarkanj B, Has-Schön E, Rajković V. Synthesis and antioxidant activity of some 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. Fused Heterocycles: Synthesis of some new imidazothiazoles. Heterocycl Com. 2002; 8(5): 433-438.
  • [41] Kuhmstedt H, Kottke K, Knoke D, Robert JF, Panouse JJ. Synthesis of amides and heterocyclic acylhydrazides with potential immunomodulator properties. Ann Pharm Fr. 1982; 40: 425-429.
  • [42] Krečmerová M, Holý A, Pohl R, Masojidková M, Andrei G, Naesens L, Neyts J, Balzarini J, De Clercq E, Snoeck R. 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, Xicluna A, Panouse JJ, Seilles E, Robert JF. Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD2-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles. Eur J Med Chem. 1994; 29(4): 309-315.
  • [44] Ulusoy N, Çapan G, Ergenç N, Ötük Sanış G, Kiraz M, Kaya D. Synthesis and antimicrobial activity of novel imidazo[2,1-b]thiazolylacetylamino/hydrazono 4-thiazolidinones. Acta Pharm Turc 1997(4); 39: 181-186.
  • [45] Çapan G, Ulusoy N, Ergenç N, Kiraz M. New 6-phenylimidazo[2,1-b]thiazole derivatives: Synthesis and antifungal activity. Monatsh Chem. 1999; 130(11): 1399-1407.
  • [46] Vanderlinden E, Göktas F¸ Cesur Z, Froeyen M, Reed ML, Russell CJ, Cesur N, Naesens L, Novel inhibitors of Influenza virus fusion: Structure-activity relationship and interaction with the viral hemagglutinin. J Virol. 2010; 84(9): 4277–4288.
APA Ulusoy Güzeldemirci N, Pehlivan E, NAESENS L (2018). Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. , 237 - 248. 10.12991/mpj.2018.61
Chicago Ulusoy Güzeldemirci Nuray,Pehlivan Erkan,NAESENS Lieve Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. (2018): 237 - 248. 10.12991/mpj.2018.61
MLA Ulusoy Güzeldemirci Nuray,Pehlivan Erkan,NAESENS Lieve Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. , 2018, ss.237 - 248. 10.12991/mpj.2018.61
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. . 2018; 237 - 248. 10.12991/mpj.2018.61
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. . 2018; 237 - 248. 10.12991/mpj.2018.61
IEEE Ulusoy Güzeldemirci N,Pehlivan E,NAESENS L "Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety." , ss.237 - 248, 2018. 10.12991/mpj.2018.61
ISNAD Ulusoy Güzeldemirci, Nuray vd. "Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety". (2018), 237-248. https://doi.org/10.12991/mpj.2018.61
APA Ulusoy Güzeldemirci N, Pehlivan E, NAESENS L (2018). Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Marmara Pharmaceutical Journal, 22(2), 237 - 248. 10.12991/mpj.2018.61
Chicago Ulusoy Güzeldemirci Nuray,Pehlivan Erkan,NAESENS Lieve Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Marmara Pharmaceutical Journal 22, no.2 (2018): 237 - 248. 10.12991/mpj.2018.61
MLA Ulusoy Güzeldemirci Nuray,Pehlivan Erkan,NAESENS Lieve Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Marmara Pharmaceutical Journal, vol.22, no.2, 2018, ss.237 - 248. 10.12991/mpj.2018.61
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. Marmara Pharmaceutical Journal. 2018; 22(2): 237 - 248. 10.12991/mpj.2018.61
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. Marmara Pharmaceutical Journal. 2018; 22(2): 237 - 248. 10.12991/mpj.2018.61
IEEE Ulusoy Güzeldemirci N,Pehlivan E,NAESENS L "Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety." Marmara Pharmaceutical Journal, 22, ss.237 - 248, 2018. 10.12991/mpj.2018.61
ISNAD Ulusoy Güzeldemirci, Nuray vd. "Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety". Marmara Pharmaceutical Journal 22/2 (2018), 237-248. https://doi.org/10.12991/mpj.2018.61