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 rong class="boldFont">4arong>-rong class="boldFont">4mrong> in moderate to good yields. Lipoxygenase inhibition of newly formed sulfonamide derivatives was investigated and some of these compounds rong class="boldFont">4mrong>, rong class="boldFont">4grong>, rong class="boldFont">4erong>, rong class="boldFont">4frong> and rong class="boldFont">4jrong> 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.