5-Methyl-4-thiazolidinones: Synthesis and evaluation as antitubercular agents

Year 2020, Volume: 24 Issue: 1, 30 - 37, 27.06.2025

Ahmet Serhat Ekinci Jan Moncol Siva Krishna Vagolu , Sriram Dharmarajan , Keriman Ozadalı Sarı

https://doi.org/10.35333/jrp.2020.110

Cited By: 5

Abstract

This paper reports the synthesis, characterization and evaluation of some 5-methyl-4-thiazolidinone derivatives for their in vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv strain by microplate alamar blue assay. Also the crystal structures of the compounds (2a and 2c) were determined by the single-crystal Xray diffraction study. Among the target compounds, 2-(4-ethoxyphenyl)-5-methyl-3-(phenylamino)thiazolidin-4-one (2g) was promising with a minimum inhibitory concentration of 12.5 μg/mL against M. tuberculosis. Based on the preliminary results, 2g was considered as a lead compound for further optimization of antimycobacterial activity.

Keywords

Antimycobacterial , tuberculosis , 4-thiazolidinone , single-crystal X-ray diffraction

References

• [1] WHO Global tuberculosis report 2018. https://www.who.int/tb/publications/global_report/en/, (accessed October 02, 2019).
• [2] Jonas da Silva S, Joel Jones J, Flavia MdS. 1,3-Thiazolidin-4-ones: Biological potential, history, synthetic development and green methodologies. Curr Org Synth. 2018; 15(8): 1109-1123. [CrossRef]
• [3] Ekinci D, Fidan İ, Durdagi S, Kaban Ş, Supuran CT. Kinetic and in silico analysis of thiazolidin-based inhibitors of α-carbonic anhydrase isoenzymes. J Enzym Inhib Med Ch. 2013; 28(2): 370-374. [CrossRef]
• [4] Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK. 4-Thiazolidinones: The advances continue…. Eur J Med Chem. 2014; 72: 52-77. [CrossRef]
• [5] 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. [CrossRef]
• [6] Verma A, Saraf SK. 4-Thiazolidinone–A biologically active scaffold. Eur J Med Chem. 2008; 43(5): 897-905. [CrossRef]
• [7] Chitre TS, Asgaonkar KD, Miniyar PB, Dharme AB, Arkile MA, Yeware A, et al. Synthesis and docking studies of pyrazine–thiazolidinone hybrid scaffold targeting dormant tuberculosis. Bioorg Med Chem Lett. 2016; 26(9): 2224- 2228. [CrossRef]
• [8] Güzel Ö, Salman A. Synthesis and biological evaluation of new 4-thiazolidinone derivatives. J Enzym Inhib Med Ch. 2009; 24(4): 1015-1023. [CrossRef]
• [9] Bhat MA. Synthesis and anti-mycobacterial activity of new 4-thiazolidinone and 1,3,4-oxadiazole derivatives of isoniazid. Acta Pol Pharm. 2014; 71(5): 763-770.
• [10] Tejeswara Rao A, Naresh Kumar K, Venkanna B, Srinubabu M, Manojit P, Jaya Shree A. Synthesis and antibacterial/antitubercular/antioxidant activities of compounds containing fluoroquinolone ring linked to a 4- thiazolidinone moiety. Lett Drug Des Discov. 2018; 15(10): 1087-1094. [CrossRef]
• [11] Deshmukh AR, Dhumal ST, Nawale LU, Khedkar VM, Sarkar D, Mane RA. Dicationic liquid mediated synthesis of tetrazoloquinolinyl methoxy phenyl 4-thiazolidinones and their antibacterial and antitubercular evaluation. Synthetic Commun. 2019; 49(4): 587-601. [CrossRef]
• [12] Jaju S, Palkar M, Maddi V, Ronad P, Mamledesai S, Satyanarayana D, et al. Synthesis and antimycobacterial activity of a novel series of isonicotinylhydrazide derivatives. Arch Pharm. 2009; 342(12): 723-731. [CrossRef]
• [13] El Bialy SA, Nagy MM, Abdel-Rahman HM. Efficient regioselective three-component domino synthesis of 3-(1,2,4- triazol-5-yl)-1,3-thiazolidin-4-ones as potent antifungal and antituberculosis agents. Arch Pharm. 2011; 344(12): 821- 829. [CrossRef]
• [14] Cihan-Üstündağ G, Şatana D, Özhan G, Çapan G. Indole-based hydrazide-hydrazones and 4-thiazolidinones: synthesis and evaluation as antitubercular and anticancer agents. J Enzym Inh Med Ch. 2016; 31(3): 369-380. [CrossRef]
• [15] Unsal-Tan O, Ozadali K, Piskin K, Balkan A. Molecular modeling, synthesis and screening of some new 4- thiazolidinone derivatives with promising selective COX-2 inhibitory activity. Eur J Med Chem. 2012; 57: 59-64. [CrossRef]
• [16] Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. OLEX2: a complete structure solution, refinement and analysis program. J Appl Crystallogr. 2009; 42(2): 339-341. [CrossRef]
• [17] Sheldrick G. SHELXT-Integrated space-group and crystal-structure determination. Acta Crystall A. 2015; 71(1): 3-8. [CrossRef]
• [18] Sheldrick G. Crystal structure refinement with SHELXL. Acta Crystall C. 2015;71(1):3-8. [CrossRef]
• [19] Nagalakshmi G, Maity T, Maiti B. Synthesis, characterization and anti-HIV evaluation of some novel 2- (substitutedphenyl)-5-methyl-3-(phenylamino)-1,3-thiazolidin-4-ones. Int J Chem Tech Res. 2013; 5(5): 2068-2078.
• [20] Collins L, Franzblau SG. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Ch. 1997; 41(5): 1004-1009. [CrossRef]