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

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 24 h).

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