Synthesis, anti-toxoplasma gondii and antimicrobial activities of 2-hydrazolyl-3-phenyl-5-(4-nitrobenzylidene)-4-thiazolidinone substituted derivatives

Abstract

A novel series of 2-hydrazolyl-3-phenyl-5-(4-nitrobenzylidene)-4-thiazolidinone substituted (3a-p) has been synthesized. The intermediates 2-hydrazolyl-3-phenyl-4-thiazolidinone substituted (2a-p) were prepared by condensation of benzaldehyde 4-phenyl-3-thiosemicarbazone substituted (1a-p) with ethyl chloroacetate. Theses intermediates were submitted to reaction with ethyl 2-cyano-3-(4-nitrophenyl)-acetate to give the title compounds. The 4-thiazolidinones were screened for their anti-Toxoplasma gondii, and all derivatives promoted decrease of percentage of infection of Vero cells, with elimination of intracellular tachyzoites. The LD50 ranged around 0.5 mM for the intracellular parasites and were higher than 10 mM for Vero cells. According to results of antimicrobial activity, only two compounds showed significant inhibition against M. luteus, but demonstrated higher values of MIC and MBC when compared with standard drug.