Abstract

SYNTHESIS, ANTIMICROBIAL AND ANTIOXIDANT EVALUATION OF 3-(2-(4-FLUOROBENZYLTHIO) PYRIMIDIN-4-YL-AMINO)-2-(3- SUBSTITUTED PHENYL) THIAZOLIDIN-4-ONES

Naganna M Goudgaon* and Rohini Y Reddy

ABSTRACT

A series of novel 3-(2-(4-fluorobenzylthio)pyrimidin-4-ylamino)-2-(3- substituted phenyl)thiazolidin-4-one analogues (6a-i) were synthesized starting from 2-thiouracil (1). Reaction of compound 1 with 4- fluorobenzylchloride gave 2-(4-fluorobenzylthio) pyrimidin-4(3H)-one (2) which on chlorination with POCl3 yielded 2-(4-fluorobenzylthio)- 4-chloropyrimidine (3). Further reaction of compound 3 with hydrazine hydrate generated the key intermediate 1-(2-(4- fluorobenzylthio)pyrimidin-4-yl)hydrazine (4). Reaction of compound 4 with appropriate substituted aromatic aldehydes furnished 2- (substituted benzylidene)-1-(2-(4-fluorobenzylthio)pyrimidin-4-yl) hydrazine (5a-i), which on further cyclisation with thioglycolic acid in dry benzene furnished 3-(2-(4-fluorobenzylthio)pyrimidin-4-ylamino)-2-(3-substituted phenyl)thiazolidin-4-one analogues (6a-i). Structural assignments of the synthesized compounds were based on their IR, 1H NMR, Mass and analytical data. All the synthesized compounds 5a-i and 6a-i were screened for their preliminary antimicrobial and antioxidant properties. Some of the compounds exhibited promising antimicrobial and antioxidant activities.

Keywords: Pyrimidines, thiazolidinones, antibacterial, antifungal, antioxidant activity.