4-(5-(4-bromophenyl)-2-methyl-4-thioxo-3,4-dihydropyrrolo(2,3-d)pyrimidin-7-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(5-(4-bromophenyl)-2-methyl-4-thioxo-3,4-dihydropyrrolo(2,3-d)pyrimidin-7-yl)benzenesulfonamide
• 英文别名: 4-[5-(4-bromophenyl)-2-methyl-4-sulfanylidene-1H-pyrrolo[2,3-d]pyrimidin-7-yl]benzenesulfonamide
• 化学式: C₁₉H₁₅BrN₄O₂S₂
• 分子量: 475.39
• InChiKey: SFEUWZWDJUJKQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(2-(4-bromophenyl)-2-oxoethylamino)benzenesulfonamide 在 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 N-(4-(4-bromophenyl)-3-cyano-1-(4-sulfamoyl)-1H-pyrrol-2-yl)ethanimidothioic acid 、 4-(5-(4-bromophenyl)-2-methyl-4-thioxo-3,4-dihydropyrrolo(2,3-d)pyrimidin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Novel sulfonamides bearing pyrrole and pyrrolopyrimidine moieties as carbonic anhydrase inhibitors: Synthesis, cytotoxic activity and molecular modeling

  摘要：

  Novel pyrrole and pyrrolopyrimidine scaffold-based sulfonamides were designed and synthesized. The carbonic anhydrase (CA) inhibition ability of all derivatives was assessed against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated isoforms hCA IX and XII. Some of these sulfonamides were 6-8 fold more potent than the reference drug acetazolamide (AZA, K-i = 5.7 nM)) against hCA XII showing subnanomolar activity. The in vitro cytotoxicity of these derivatives was evaluated against MCF-7, where some derivatives were more cytotoxic than doxorubicin (IC50 = 8.02 mu M) displaying IC50 values between 6.46 and 7.56 mu M. Docking of these sulfonamides with CA XII was performed and their binding modes were comparable with that of AZA. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.059

文献信息

• Novel sulfonamides bearing pyrrole and pyrrolopyrimidine moieties as carbonic anhydrase inhibitors: Synthesis, cytotoxic activity and molecular modeling
  作者：Mostafa M. Ghorab、Mariangela Ceruso、Mansour S. Alsaid、Yassin M. Nissan、Reem K. Arafa、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2014.09.059

  日期：2014.11

  Novel pyrrole and pyrrolopyrimidine scaffold-based sulfonamides were designed and synthesized. The carbonic anhydrase (CA) inhibition ability of all derivatives was assessed against the human (h) cytosolic isoforms hCA I and II and the transmembrane, tumor-associated isoforms hCA IX and XII. Some of these sulfonamides were 6-8 fold more potent than the reference drug acetazolamide (AZA, K-i = 5.7 nM)) against hCA XII showing subnanomolar activity. The in vitro cytotoxicity of these derivatives was evaluated against MCF-7, where some derivatives were more cytotoxic than doxorubicin (IC50 = 8.02 mu M) displaying IC50 values between 6.46 and 7.56 mu M. Docking of these sulfonamides with CA XII was performed and their binding modes were comparable with that of AZA. (C) 2014 Elsevier Masson SAS. All rights reserved.