Synthesis of new sulfonamides as lipoxygenase inhibitors

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• 作者：Ghulam Mustafa^a ; ^{gmustafa884@yahoo.com} ; Islam Ullah Khan^a ; ^{iuklodhi@yahoo.com} ; Muhammad Ashraf^b ; ^c ; Iftikhar Afzal^c ; Sohail Anjum Shahzad^d ; Muhammad Shafiq^a
• 关键词：LDNFKAHBKBKFAC-UHFFFAOYSA-N
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2012
• 期刊代码：9_09680896
• 类别：ch
• 出版时间：15 April, 2012
• 卷：20
• 期：8
• 页码：2535-2539
• 文件大小：319 K

摘要

The present study describes a convenient method for the synthesis of new lipoxygenase inhibitors, 4-(toluene-4-sulfonylamino)-benzoic acids from p-amino benzoic acid. Reaction of p-amino benzoic acid with p-toluenesulfonyl chloride provided thirteen N- and O-alkylation products 4a-4m in moderate to good yields. Lipoxygenase inhibition of newly formed sulfonamide derivatives was investigated and some of these compounds 4m, 4g, 4e, 4f and 4j showed good lipoxygenase inhibitory activities with IC₅₀ values ranged between 15.8 卤 0.57 and 91.7 卤 0.61 渭mol whilst all other compounds exhibited mild anti-lipoxygenase activities with IC₅₀ values ranged between 139.2 卤 0.75 and 232.1 卤 0.78 渭mol. N-alkylated products were more active against the enzyme than O-alkylated or both N- and O-alkylated ones. All synthesized sulfonamides were recrystallized in chloroform to give these title compounds which were characterized using FTIR, ¹H NMR, ¹³C NMR, elemental analysis and single crystal X-ray diffraction techniques.