4-(toluene-4-sulfonylamino)-benzoic acid cyanomethyl ester | 1373444-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(toluene-4-sulfonylamino)-benzoic acid cyanomethyl ester
• 英文别名: Cyanomethyl 4-(4-methylbenzenesulfonamido)benzoate；cyanomethyl 4-[(4-methylphenyl)sulfonylamino]benzoate
• CAS: 1373444-86-0
• 化学式: C₁₆H₁₄N₂O₄S
• 分子量: 330.364
• InChiKey: FWHZGCPCQPNJJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氨基苯甲酸 在 sodium hydride 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 4-(toluene-4-sulfonylamino)-benzoic acid cyanomethyl ester
  参考文献：
  名称：

  Synthesis of new sulfonamides as lipoxygenase inhibitors

  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 +/- 0.57 and 91.7 +/- 0.61 mu mol whilst all other compounds exhibited mild anti-lipoxygenase activities with IC50 values ranged between 139.2 +/- 0.75 and 232.1 +/- 0.78 mu 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, H-1 NMR, C-13 NMR, elemental analysis and single crystal X-ray diffraction techniques. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.055

文献信息

• Synthesis of new sulfonamides as lipoxygenase inhibitors
  作者：Ghulam Mustafa、Islam Ullah Khan、Muhammad Ashraf、Iftikhar Afzal、Sohail Anjum Shahzad、Muhammad Shafiq

  DOI：10.1016/j.bmc.2012.02.055

  日期：2012.4

  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 +/- 0.57 and 91.7 +/- 0.61 mu mol whilst all other compounds exhibited mild anti-lipoxygenase activities with IC50 values ranged between 139.2 +/- 0.75 and 232.1 +/- 0.78 mu 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, H-1 NMR, C-13 NMR, elemental analysis and single crystal X-ray diffraction techniques. (C) 2012 Elsevier Ltd. All rights reserved.