4-(5-methyl-2-oxoindolin-3-ylideneamino)-N-(4-sulfamoylphenyl)benzamide

• 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-(5-methyl-2-oxoindolin-3-ylideneamino)-N-(4-sulfamoylphenyl)benzamide
• 英文别名: 4-[(5-methyl-2-oxo-1H-indol-3-ylidene)amino]-N-(4-sulfamoylphenyl)benzamide
• 化学式: C₂₂H₁₈N₄O₄S
• 分子量: 434.475
• InChiKey: AETBZXKNLNTEJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-(氨基磺酰基)苯基)-4-硝基苯甲酰胺 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 4-(5-methyl-2-oxoindolin-3-ylideneamino)-N-(4-sulfamoylphenyl)benzamide
  参考文献：
  名称：

  Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII

  摘要：

  By using a molecular hybridization approach, two series of amido/ureidosubstituted benzenesulfonamides incorporating substituted-isatin moieties were synthesized. The prepared derivatives were in vitro evaluated for their inhibitory activity against human carbonic anhydrase (hCA, EC 4.2.1.1) I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms. All these isoforms were inhibited in variable degrees by the sulfonamides reported here. hCA I was inhibited with K(I)s in the range of 7.9-894 nM, hCA II in the range of 7.5-1645 nM (with one compound having a K-I > 10 mu M); hCA IX in the range of 5.0-240 nM, whereas hCA XII in the range of 0.47-2.83 nM. As all these isoforms are involved in various pathologies, in which their inhibition can be exploited therapeutically, the derivatives reported here may represent interesting extensions to the field of CA inhibitors of the sulfonamide type. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.030

文献信息

• Amido/ureidosubstituted benzenesulfonamides-isatin conjugates as low nanomolar/subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform XII
  作者：Wagdy M. Eldehna、Mohamed Fares、Mariangela Ceruso、Hazem A. Ghabbour、Sahar M. Abou-Seri、Hatem A. Abdel-Aziz、Dalal A. Abou El Ella、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2016.01.030

  日期：2016.3

  By using a molecular hybridization approach, two series of amido/ureidosubstituted benzenesulfonamides incorporating substituted-isatin moieties were synthesized. The prepared derivatives were in vitro evaluated for their inhibitory activity against human carbonic anhydrase (hCA, EC 4.2.1.1) I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms. All these isoforms were inhibited in variable degrees by the sulfonamides reported here. hCA I was inhibited with K(I)s in the range of 7.9-894 nM, hCA II in the range of 7.5-1645 nM (with one compound having a K-I > 10 mu M); hCA IX in the range of 5.0-240 nM, whereas hCA XII in the range of 0.47-2.83 nM. As all these isoforms are involved in various pathologies, in which their inhibition can be exploited therapeutically, the derivatives reported here may represent interesting extensions to the field of CA inhibitors of the sulfonamide type. (C) 2016 Elsevier Masson SAS. All rights reserved.