SYNTHESIS AND BIOLOGICAL EVALUATION OF COUMARIN CLUBBED OXAZINES

Coumarin segment have been reported broad spectrum of different biological activities with the oxazine derivatives. In view that we have synthesized newer coumarin clubbed 4-(4-fluorophenyl)-6-substituted phenyl-2H-1,3-oxazin-2-amine and screened for their biological studies. 4-(4-fluorophenyl)-6-substituted phenyl-2H-1,3-oxazin-2-amine IIa-j condensed with 4-Methyl-6-nitro-2-oxo-2H-chromen-7-yl chloro acetate 5 to afford 4-Methyl-6-nitro-2-oxo-2H-chromen-7-yl-2-(4-(4-sustitutedphenyl) oxazine – 2-  yl – amino) acetates 2a-j. The newer compounds were characterized by IR, NMR and mass spectral studies and were screened for their antimicrobial, antitubercular and antioxidant activities. Compound 2a (-C₆H₅) 62.5 µg/ml, 2d (2-OH) 100 µg/ml against S. aureus, 2a (-C₆H₅) 50 µg/ml, 2f (4-F) and 2j (3-OPh) 100 µg/ml against S. pyogenes as compared to chloramphenicol and the other compound 2c (4-Cl) showed excellent potency 25 µg/ml against E. coli and 12.5 µg/ml against P. aeruginosa while compound 2e (4-OH) exhibited comparable activity of 62.5 µg/ml and 100 µg/ml against E. coli and P. areuginosa respectively. Furthermore 2i (3-Br) also showed 100 µg/ml moderate potency against E. coli compared to the standard drugs chloramphenicol and ciprofloxacin. The study of antifungal activity indicates that 2i (3-Br) showed remarkable potency of 250 µg/ml against C. albicans and compounds 2a (-C₆H₅), 2b (2-Cl), 2c (4-Cl), 2f (4-F) and 2j (3-OPh) exhibited comparable activity of 500 µg/ml against C. albicans when compared to the standard drug Griseofulvin.