A Synthetic Approach, Characterization and Biological Evaluation of Novel 5-(Arylidene)-2-(5-methyl-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one Derivatives

Abstract

The extensive biological potential of thiazolidin-4-one and 1,3,4-thiadiazole moieties, the novel string of 5-(arylidene)-2-(5-methyl-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one has been synthesized and characterized. The synthesized derivatives were screened for antimicrobial potential using serial tube dilution method. The results showed that all the synthesized compounds have significant biological activity against the microorganisms being tested. The antimicrobial activity of the compounds TA₂, TA₃, TA₄, TA₉, TA₁₀ and TA₂₀ against the tested microbial strains was promising. Compound TA₄ (2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)-5-(4-nitrobenzylidene)thiazolidin-4-one) and TA₂ (5-(4-chlorobenzylidene)-2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one) showed promising antimicrobial activity against microbial strains. Compound TA₉ (5-(4-(benzyloxy)benzylidene)-2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one) was found to be the most effective towards B. subtilis. Compound TA₁₀ (5-(3,4-dimethoxybenzylidene)-2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one) was discovered to be the most potent against the Gram-negative bacteria. Compounds TA₃ (5-(4-bromobenzylidene)-2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one) and TA₂₀ (5-(2-bromobenzylidene)-2-((5-methyl-1,3,4-thiadiazol-2-yl)imino)thiazolidin-4-one) were the most effective compounds against the fungal strain.