Abstract

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF 6-AMINO-5-[2-(5-SUBSTITUTED-2-PHENYL-1HINDOL- 3-YL)-4-OXOTHIAZOLIDIN-3-YL]-1,3- DIMETHYLPYRIMIDINE-2,4-DIONE

Saundane Anand R* and Kalpana Rayappa

ABSTRACT

This work describes the synthesis and biological activities of 6-amino- 5-[2-(5-substituted-2-phenyl-1H-indol-3-yl)-4-oxothiazolidin-3-yl]- 1,3-dimethylpyrimidine-2,4-dione (4a-c) which is prepared from 6- amino-5-(5-substituted-2-phenyl-1H-indol-3-yl)methyleneamino-1,3- dimethylpyrimidine-2,4-diones (3a-c). The structure of all the newly synthesized compounds is confirmed by their elemental analysis, IR, 1H &13C NMR and mass spectral studies. These compounds are screened for their antimicrobial, antitubercular, antioxidant and cytotoxic activities. Compound 4c exhibited the maximum zone of inhibition against the bacteria S. aureus and P. aeurogenosa and the fungi A. flavus. Compounds 3a and 4b (MIC-3.125 μg/ml) exhibited promising antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Compound 4c exhibited good radical scavenging activity compared with standard at concentration 25 μg/ml. Compound 4b exhibited maximum ferric ion reducing ability. Compounds 3b and 4c exhibited 100 % cell lysis at concentration 10 μg/ml against MDA-MB-231 (Human adenocarcinoma mammary gland) cell line (IC50<10 μg/ml).

Keywords: 1,3-dimethyluracil, 2-phenylindole, 1,3-thiazolidin-4-one, antioxidant, antitubercular and cytotoxic activities.