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

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.

Synthetic strategies and medicinal perspectives of 4‐thiazolidinones: Recent developments and structure–activity relationship studies

“…It was concluded that ethyl substituted phenyl rings at position 2 of the thiazolidinone scaffold provided the highest activity, while methyl substitution on phenyl rings led to a deterioration of antimycobacterial potential. Also, the replacement of the phenyl ring with a thienyl or pyridyl moiety in the thiazolidinone nucleus did not increase the activity [32].…”

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

“…All most active compounds contain halogen substituent in 2-phenyl group at ortho or para positions. A series of 2-aryl-5-methylthiazolidin-4-ones was synthesized by Ekinci et al All compounds of this series were evaluated for antimycobacterial activity in vitro against M. tuberculosis H37Rv strain by microplate alamar blue assay (MABA) [148]. Only Compound 147 (Figure 55) with 2-(4-ethylphenyl) substituent showed moderate antimycobacterial effect with MIC = 12.5 µg/mL.…”

2,3,5‐Trisubstituted Thiazolidinone Derivatives as Potential Antimicrobial and Antitubercular Agents and In Silico Studies

“…[9] It is remarkable that thiazole and thiazolidinone derivatives possess a broad spectrum of biological activity such as antimicrobial, [10][11][12][13][14] anti-inflammatory, [15] anticancer, [16][17][18] antidiabetic, [19] antitubercular, [20][21][22][23] anticandidal, [24] leishmanicidal, [25] allosteric glucokinase activator, [26] antiproliferative, [27] wound healing, [28] antibiofilm, [29] anticonvulsant [30] etc. Further search for the thiazolidinone based compounds envisaged the compounds (1), ( 2) and (3) as promising antimicrobial [31][32][33] as well as ( 4) and (5) as antitubercular [34][35] agents (Figure 1). Thus it is worth exploring derivatives of thiazolidinones for their antimicrobial and antitubercular activities.…”