Synthesis and biological evaluation of some 2H-3-(5'-substituted-2'-phenylindol-3'-yl)-3-4-dihydro-6-substituted-1,3-benzoxazines and 1-(3',5'-disubstituted indol-2'-yl)-3-(5'-substituted-2'-phenylindol-3'-yl)-2,3-dihydro-2-oxo-4,6(1H,5H)-pyrimidinediones

Abstract

2-(5'-Substituted-2'-phenylindol-3'-imino)-5-substituted methylphenols (IIIa-i) on reduction with sodium borohydride followed by treatment with formaldehyde yielded respective-2H-(5'-substituted-2'-phenylindol-3'-yl)-3,4-dihydro-6-substituted-1,3-benzoxazines (Va-i). 1-(3',5'-Disubstituted indol-2'-yl)-3-(5-substituted-2'-phenylindol-3'-yl) ureas (VIIa-o) were synthesised by the reaction of la-c with 3,5-disubstituted indole-2-carboxy azides (Vla-e), while (VIIa-o) on treatment with diethyl malonate in the presence of sodium ethoxide afforded 1-(3'-5'-disubstituted indol-2'-yl)-3-(5'-substituted-2'-phenylindol-3'-yl)-2,3-dihydro-2-oxo-4,6-(1H,5H) pyrimidinediones (VIIIa-o). All these compounds have been tested for their antibacterial activity against E. coli, S. aureus and P. vulgaris and antifungal activity against A. niger and C. albicans. Compounds (VIIIa-o) were screened for their analgesic activity, some of the compounds showed good antibacterial, antifungal and analgesic activity.