Girgis Adel S, Ellithey Mohey
Pesticide Chemistry Department, National Research Centre, Dokki, 12622 Cairo, Egypt.
Bioorg Med Chem. 2006 Dec 15;14(24):8527-32. doi: 10.1016/j.bmc.2006.08.032. Epub 2006 Sep 14.
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).
通过伯胺8或仲胺6对双恶唑-5(4H)-酮5进行亲核进攻，合成了多种N,N'-双{2-[1,2-乙二基双(氧基-2,1-亚苯基)]-1-(取代羰基)乙烯基}苯甲酰胺7a - c、9a - d。后者是通过2,2'-[1,2-乙二基双(氧基)]双苯甲醛(4)与马尿酸在乙酸酐中，于无水醋酸钠存在下反应制得。使用角叉菜胶诱导的大鼠足爪水肿模型，对所制备化合物的抗炎特性进行筛选。许多所制备的含双苯甲酰胺化合物显示出相当可观的体内抗炎活性，尤其是7b，在连续时间间隔(1、2、3、4和24小时)显示出与酮洛芬(用作参考标准)相当的显著药理特性。
