Synthesis and pharmacological activity of 2H-3-(various substituted indol-2 '-carboxamidyl)-3,4-dihydro-1,3-benzoxazines and 2H-3-(2 ',5 '-disubstituted indol-3 '-yl)methyl-1,3-benzoxazoles

Abstract

2H-3-(Various substituted indol-2'-carboxamidylimino)-5-substituted methylphenols 3a-m obtained by the reaction of appropriately substituted indole-2-carboxyhydrazides la-h and 5-substituted salicylaldehydes 2a and b, on reduction with sodium borohydride followed by treatment with formaldehyde yield respective 2H-3-(various substituted indol-2'-carboxamidyl)-3,4-dihydro-1,3-benzoxazines 5a-m. 2-(2',5'-Disubstituted indol-3'-yl)methyliminophenols 8a-d have been synthesised by reacting 2,5-disubstituted indol-3-carboxaldehydes 6a-d with o-aminophenol 7. Compounds 8a-d when reduced with sodium borohydride and subsequent treatment with formaldehyde yield the desired 2H-3-(2',5'-disubstituted indol-3'-yl)methyl-1,3-benzoxazoles 10a-d. All the newly synthesised compounds have been tested for their antimicrobial activity against E.coli, S.aureus, P.vulgaris and A.niger. Compounds 5a-f and 10a-d have been screened for their anticatatonic and analgesic activities. Only compounds 5d, 5e and 10d are found to exhibit good anticatatonic activity and compounds 5e and 10a show good analgesic activity.