Synthesis and biological activity of 4-thiazolidinone derivatives of phenothiazine

Abstract

A new series of N-[3-(10H-phenothiazin-10-yl)propyl]-2-(substituted phenyl)-4-oxo-5-(substituted benzylidene)-3-thiazolidinecarboxamide, 5a-s were synthesized. The reaction of thioglycolic acid with N-[3-(10H-phenothiazin- 10-yl)propyl]-N'-[(substituted phenyl)methylidene]urea, 3a-s in the presence of anhydrous ZnCl2 afforded the new heterocyclic compounds N-[3- -(10H-phenothiazin-10-yl)propyl]-2-(substituted phenyl)-4-oxo-3- thiazolidinecarboxamide, 4a-s. The latter product on treatment with several selected substituted aromatic aldehydes in the presence of C2H5ONa underwent the Knoevenagel reaction to yield 5a-s. The structure of compounds 1, 2, 3a-s, 4a-s and 5a-s were confirmed by IR, 1H-NMR, 13C-NMR and FAB mass spectroscopy and by chemical analysis. All the above compounds were screened for their antimicrobial activity against some selected bacteria and fungi and for their antituberculosis activity, the compounds were screened against the bacterium Mycobacterium tuberculosis. Copyright 2012 (CC) SCS.