Abstract

SYNTHESIS AND EVALUATION OF NOVEL N-([1,3,4] OXADIAZINO [6,5]INDOL- 2-YL-METHYL)-4-(BENZOXAZOL-2-YL)ANILINES AS ANTI-INFLAMMATORY AND ANTI-OXIDANT ACTIVITY

Kalpana Devi Gangavath, Sammaiah Gade and Sarangapani Manda*

ABSTRACT

A new series of N-([1,3,4]oxadiazino [6,5]indol-2-yl-methyl)-4-(benzoxazol-2-yl)anilines (IXa-o) were synthesized and their structures were characterized by spectral data. All newly synthesized compounds were evaluated for their anti-inflammatory activity via In vitro COX-2 inhibition and In vivo carrageenan induced paw methods. In vivo study was done at a dose of 100mg/kg body weight(p.o). Oxadiazino[6,5]indole fused benzoxazole derivatives (IXa-o) have shown In vitro anti-inflammation activity ranging between 32.6%−58.2%. Compound IXm showed equipotent anti-inflammation activity 32.62±0.23 compared to reference drug Indomethacin 28.41±0.19 respectively. Structure-activity relationship (SAR) studies revealed that the presence of the electron-attracting chloro, bromo, flouro substituent at position-6th and position-8th of the Oxadiazino-indole moiety played an important role in enhancing the anti-inflammatory potential of the synthesized compounds N-([1,3,4]oxadiazino[6,5]indol-2-ylmethyl)-4-(benzoxazol-2-yl)anilines (IXa-o). Compound with 6-flouro 7-Chloro moiety was found to be the potent anti-inflammatory and anti-oxidant activity. Introduction of methyl and nitro groups on the indole moiety resulted in decreasing the anti-inflammatory activity and antioxidant activity.

Keywords: Anti-inflammatory activity, Indole, Benzoxazole, Carrageenan, Indomethacin.