SYNTHESIS AND ANTIOXIDANT ACTIVITY OF SOME CHALCONES CONTAINING N-ARYLACETAMIDE GROUP

Abstract

(E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (3a) or (E)-3-(4-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (3b) were prepared from reaction of 4-hydroxyacetophenone (1) and 4-chlorobenzaldehyde (2a) or 4-methoxybenzaldehyde (2b), respectively. The reaction of 3a or 3b and various N-aryl-2-chloroacetamides (4a-d) afforded eight new N-aryl-2-(4-(3-(4substituted phenyl)acryloyl)phenoxy)acetamide compounds (5a-h). The structures of the compounds were confirmed by IR, H-NMR, C-NMR and HR-MS spectral data. Antioxidant activity performed by DPPH radical scavenging method showed that N-aryl-2-(4-(3-(4-substituted phenyl)acryloyl)phenoxy)acetamide compounds (5a-h) at a concentration of 10.0 μg/ mL possess antioxidant activity in equivalent to that of ascorbic acid at a concentration of 6.0-8.0 μg/ mL while the antioxidant activity of 3a and 3b compounds is higher that of ascorbic acid at the same concentration.