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一些含苯磺酰胺的新型1,3,5-三取代吡唑啉的合成与抗炎活性

Synthesis and antiinflammatory activity of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide.

作者信息

Rathish I G, Javed Kalim, Ahmad Shamim, Bano Sameena, Alam M S, Pillai K K, Singh Surender, Bagchi Vivek

机构信息

Department of Chemistry, Faculty of Science, Jamia Hamdard Hamdard University, New Delhi, India.

出版信息

Bioorg Med Chem Lett. 2009 Jan 1;19(1):255-8. doi: 10.1016/j.bmcl.2008.10.105. Epub 2008 Oct 30.

Abstract

Nineteen new 2-pyrazoline bearing benzenesulfonamide derivatives were synthesized by condensing chalcones with 4-hydrazinonbenzenesulfonamide hydrochloride. Their chemical structures were proved by means of IR, (1)H NMR, (13)C NMR, mass spectroscopic and elemental analyses data. These compounds were tested at dose of 20mg/kg for their anti-inflammatory activity in carrageenan-induced rat paw edema model and volume of paw edema was measured at 0, 3 and 5h. Two compounds 3k and 3l were found to be more active than celecoxib throughout the study (at 3 and 5h). While two other compounds 3m and 3n showed more potent activity than celecoxib at 5h. They are devoid of ulcerogenic potential when administered orally at a dose of 60 mg/kg. Compounds (3k-m) showed COX-1 and COX-2 inhibitory activity at 0.05 microM.

摘要

通过查尔酮与4-肼基苯磺酰胺盐酸盐缩合反应合成了19种新型含2-吡唑啉的苯磺酰胺衍生物。借助红外光谱、核磁共振氢谱、核磁共振碳谱、质谱和元素分析数据证实了它们的化学结构。在角叉菜胶诱导的大鼠足跖水肿模型中,以20mg/kg的剂量对这些化合物进行抗炎活性测试,并在0、3和5小时测量足跖水肿体积。在整个研究过程中(3小时和5小时),发现两种化合物3k和3l比塞来昔布更具活性。而另外两种化合物3m和3n在5小时时显示出比塞来昔布更强的活性。当以60mg/kg的剂量口服给药时,它们没有致溃疡的潜力。化合物(3k-m)在0.05微摩尔浓度下显示出COX-1和COX-2抑制活性。

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