Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives
Yıl: 2022 Cilt: 26 Sayı: 3 Sayfa Aralığı: 641 - 654 Metin Dili: İngilizce DOI: 10.29228/jrp.161 İndeks Tarihi: 08-06-2022
Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives
Öz: A series of novel 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone (2a-f), 2-(2-thienyl)-5-[(4-
bromophenyl)amino]-1,3,4-oxadiazole (3), 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone (5a-h) and 2-aryl-3-(2-
thienylcarbonyl)amino-5-methyl-4-thiazolidinone (6a-h) were designed and synthesized. The structural elucidations of
the novel compounds were performed by IR, 1H-NMR, mass and elemental analysis. The compounds were evaluated
for their antimycobacterial and antifungal activities. According to the biological activity studies activities of the
compounds, 2f (MIC: >12.5 μg/ml, 76% inhibition), 3 (MIC: >12.5 μg/ml, 43% inhibition), and 5c (MIC: >12.5 μg/ml,
38% inhibition), displayed antimycobacterial activity. 2b (MIC: 25 μg/ml) displayed antifungal activity against T.
rubrum. Besides, x-ray crystallography studies were performed to illuminate the structure of 2e. Consequently, the
obtained results relvealed that 2f, 3 and 5c present a leading structure for future drug development due to its
straightforward synthesis and relevant bioactivity.
Anahtar Kelime: Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
- [1] Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Sokovic M, Ciric A, Glamoclija J. Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem. 2010; 18(1): 426-432. [CrossRef]
- [2] 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. Turcica. 1997; 39(4), 181-186.
- [3] Ouf SA, Gomha SM, Eweis M, Ouf AS, Sharawy IA. Efficiency of newly prepared thiazole derivatives against some cutaneous fungi. Bioorg Med Chem. 2018; 26(12): 3287-3295. [CrossRef]
- [4] Samadhiya P, Sharma R, Srivastava SK, Srivastava SD. Synthesis and biological evaluation of 4-thiazolidinone derivatives as antitubercular and antimicrobial agents. Arab J Chem. 2014; 7(5): 657-665. [CrossRef]
- [5] Kaminskyy D, Bednarczyk-Cwynar B, Vasylenko O, Kazakova O, Zimenkovsky B, Zaprutko L, Lesyk R. Synthesis of new potential anticancer agents based on 4-thiazolidinone and oleanane scaffolds. Med Chem Res. 2012; 21: 3568-3580. [CrossRef]
- [6] Deep A, Jain S, Sharma PC, Phogat P, Malhotra M. Synthesis of 2-(aryl)-5-(arylidene)-4-thiazolidinone derivatives with potential analgesic and anti-inflammatory activity. Med Chem Res. 2012; 21: 1652-1659. [CrossRef]
- [7] Vigorita MG, Ottana R, Monforte F, Maccari R, Trovato A, Monforte MT, Taviano M. Synthesis and antiinflammatory, analgesic activity of 3,3’-(1,2,-Ethanediyl)-bis[2-aryl-4-thiazolidinone] chiral compounds. Part 10. Bioorganic Med Chem Lett. 2001; 11(21): 2791-2794. [CrossRef]
- [8] Gürsoy A, Terzioğlu N. Synthesis and isolation of new regioisomeric 4-thiazolidinones and their anticonvulsant activity. Turk J Chem. 2005; 29(3): 247-254.
- [9] Barbosa VA, Barea P, Mazia RS, Ueda-Nakamura T, da Costa WF, Foglio MA, Ruiz ALTG, de Carvalho JE, Vendramini-Costa DB, Nakamura CV, Sarragiotto MH. Synthesis and evaluation of novel hybrids β-carboline-4- thiazolidinones as potential antitumor and antiviral agents. Eur J Med Chem. 2016; 124: 1093-1104. [CrossRef]
- [10] Gomha SM, Khalil KD. A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules. 2012; 17(8): 9335-9347. [CrossRef]
- [11] Bhutani R, Pathak DP, Kapoor G, Husain A, Iqbal MA. Novel hybrids of benzothiazole-1,3,4-oxadiazole-4- thiazolidinone: Synthesis, in silico ADME study, molecular docking and in vivo anti-diabetic assessment. Bioorg Chem. 2019; 83: 6-19. [CrossRef]
- [12] Türe A, Ergül M, Ergül M, Altun A, Küçükgüzel İ. Design, synthesis, and anticancer activity of novel 4- thiazolidinone-phenylaminopyrimidine hybrids. Mol. Divers. 2021; 25: 1025-1050. [CrossRef]
- [13] Çakır G, Küçükgüzel İ, Guhamazumder R, Tatar E, Manvar D, Basu A, Patel BA, Zia J, Talele TT, Kaushik-Basu N. Novel 4-Thiazolidinones as Non-Nucleoside Inhibitors of Hepatitis C Virus NS5B RNA-Dependent RNA Polymerase. Arch. Pharm. 2015; 348: 10-22. [CrossRef]
- [14] 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. [CrossRef]
- [15] Tatar E, Küçükgüzel İ, De Clercq E, Şahin F, Güllüce M. Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2- (benzoylamino)-4-(methylthio)butyryl]-4-alkyl/arylalkyl thiosemicarbazides. Arkivoc. 2008; 14: 191-210. [CrossRef]
- [16] Tatar E, Küçükgüzel İ, Küçükgüzel ŞG, Yılmaz-Demircan F, De Clercq E, Andrei G, Snoeck R, Pannecouque C, Şahin F, Bayrak ÖF. Synthesis, Anti-Tuberculosis and Antiviral Activity of Novel 2-isonicotinoylhydrazono-5- arylidene-4-thiazolidinones. Int. J. Drug Discov. 2010; 1: 19-32.
- [17] Kline T, Felise HB, Barry KC, Jackson ST, Nguyen HV, Miller SI. Substituted 2-Imino-5-arylidenethiazolidin-4-one inhibitors of bacterial type III secretion. J Med Chem. 2008; 51(22): 7065-7074. [CrossRef]
- [18] Cesur N, Cesur Z, Gürsoy A. New acylthiosemicarbazides, thiazolidinones, and 1,3,4-oxadiazoles as possible anticonvulsants. Arch. Pharm. 1992; 325: 623-624.
- [19] Ashour FA, Almazroa SA. Synthesis of certaine thiosemicarbazide and triazole derivatives as potential antimicrobial agents. Farmaco. 1990; 45: 1207-1218.
- 20] Dincel ED, Ulusoy-Güzeldemirci N, Şatana D, Küçükbasmacı Ö. Design, synthesis, characterization and antimicrobial evaluation of some novel hydrazinecarbothioamide, 4-thiazolidinone and 1,2,4-triazole-3-thione derivatives. J Heterocycl Chem. 2021; 58(1): 195-205. [CrossRef]
- [21] Ulusoy N, Çapan G, Ergenç N, Ekinci AC, Vidin A. Synthesis, characterization and anticonvulsant activity of new 4-thiazolidinone and 1,2,4-triazole-3-thione derivatives. Acta Pharm. Turcica. 1998; 40(1): 5-8.
- [22] Ulusoy-Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and antiviral activity evaluation of novel 4- thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Marmara Pharm J. 2018; 22(2): 237-248. [CrossRef]
- [23] Johnson CK, ORTEP II. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA, 1976. This is an open access article which is publicly available on our journal’s website under Institutional Repository at http://dspace.marmara
| APA | DİNCEL E, Satana D, ÖZBEY S, ULUSOY-GÜZELDEMİRCİ N (2022). Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. , 641 - 654. 10.29228/jrp.161 |
| Chicago | DİNCEL Efe Doğukan,Satana Dilek,ÖZBEY Süheyla,ULUSOY-GÜZELDEMİRCİ Nuray Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. (2022): 641 - 654. 10.29228/jrp.161 |
| MLA | DİNCEL Efe Doğukan,Satana Dilek,ÖZBEY Süheyla,ULUSOY-GÜZELDEMİRCİ Nuray Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. , 2022, ss.641 - 654. 10.29228/jrp.161 |
| AMA | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. . 2022; 641 - 654. 10.29228/jrp.161 |
| Vancouver | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. . 2022; 641 - 654. 10.29228/jrp.161 |
| IEEE | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N "Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives." , ss.641 - 654, 2022. 10.29228/jrp.161 |
| ISNAD | DİNCEL, Efe Doğukan vd. "Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives". (2022), 641-654. https://doi.org/10.29228/jrp.161 |
| APA | DİNCEL E, Satana D, ÖZBEY S, ULUSOY-GÜZELDEMİRCİ N (2022). Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. Journal of research in pharmacy (online), 26(3), 641 - 654. 10.29228/jrp.161 |
| Chicago | DİNCEL Efe Doğukan,Satana Dilek,ÖZBEY Süheyla,ULUSOY-GÜZELDEMİRCİ Nuray Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. Journal of research in pharmacy (online) 26, no.3 (2022): 641 - 654. 10.29228/jrp.161 |
| MLA | DİNCEL Efe Doğukan,Satana Dilek,ÖZBEY Süheyla,ULUSOY-GÜZELDEMİRCİ Nuray Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. Journal of research in pharmacy (online), vol.26, no.3, 2022, ss.641 - 654. 10.29228/jrp.161 |
| AMA | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. Journal of research in pharmacy (online). 2022; 26(3): 641 - 654. 10.29228/jrp.161 |
| Vancouver | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives. Journal of research in pharmacy (online). 2022; 26(3): 641 - 654. 10.29228/jrp.161 |
| IEEE | DİNCEL E,Satana D,ÖZBEY S,ULUSOY-GÜZELDEMİRCİ N "Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives." Journal of research in pharmacy (online), 26, ss.641 - 654, 2022. 10.29228/jrp.161 |
| ISNAD | DİNCEL, Efe Doğukan vd. "Synthesis, characterization and antimicrobial evaluation of new 2-(2-thienylcarbonyl)hydrazono-3-alkyl/aryl-4-thiazolidinone and 2-aryl-3-(2-thienylcarbonyl)amino-4-thiazolidinone derivatives". Journal of research in pharmacy (online) 26/3 (2022), 641-654. https://doi.org/10.29228/jrp.161 |
