Facile synthesis of non-steroidal anti-inflammatory active bisbenzamide-containing compounds

Abstract

A variety of N,N'-bis{2-[1,2-ethanediylbis(oxy-2,1-phenylene)]-1-(substituted carbonyl)ethenyl}benzamides 7a-c, 9a-d were synthesized via nucleophilic attack of either primary 8 or secondary amines 6 on bisoxazol-5(4H)-one 5. The latter was obtained through the reaction of 2,2'-[1,2-ethanediylbis(oxy)]bisbenzaldehyde (4) with hippuric acid in acetic anhydride in the presence of anhydrous sodium acetate. The anti-inflammatory properties of the prepared compounds were screened using carrageenan-induced paw oedema in rats. Many of the prepared bisbenzamide-containing compounds show considerable in vivo anti-inflammatory activity, especially 7b which reveals remarkable pharmacological properties comparable with ketoprofen (which was used as a reference standard) at successive time intervals (1, 2, 3, 4 and 24h).