Synthesis and biological activities of some 5-substituted 2-phenyl-3-(6-aryl-3-cyano-2-substituted pyridin-4-yl) indoles

Abstract

3-(5?-Substituted-2?-phenyl-1 H-indol-3?-yl)-1 -phenylprop-2-en-1 -ones (2) were prepared from indole-3-carboxyaldehydes (1) and 4-substitutedacetophenones in presence of piperidine. Compounds (2) were subjected to cyclocondensation with ethyl cyanoacetate in presence of ammonium acetate to afford 2-oxo-6-phenyl-4-(5?-substituted-2?-phenyl-1H- indol-3?-yl) pyridine-3-carbonitriles (3). These compounds when treated with ethyl chloroacetate in acetone in presence of base, yielded corresponding ethyl 2-[3-cyano-6-(4.subst;tuted phenyl)-4-(5?-substituted-2?- phenyl-1/V-indol-3?-yl) pyridine-2-yloxy] acetates (4). Compounds 4 on fusion with anthranilic acid at 130° afforded 6-(4-substitutedphenyl)-2-[(4- oxo-4H-3,1-benzoxazin-2-yl) methoxy]-4-(5?-substituted-2?-phenyl-1 H-indol-3?-yl) nicotinonitriles (5). Structures of all the newly synthesized compounds were confirmed by their IR, NMR, mass spectral data and elemental analyses. These compounds were screened for their antimicrobial and antioxidant activity.