4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)benzenesulfonamide | 3821-43-0

• 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-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)benzenesulfonamide
• 英文别名: N-<4-Chlor-3-trifluormethyl-phenyl>-N'-<4-sulfamoyl-phenyl>-harnstoff；1-[4-Chloro-3-(trifluoromethyl)phenyl]-3-(4-sulfamoylphenyl)urea；1-[4-chloro-3-(trifluoromethyl)phenyl]-3-(4-sulfamoylphenyl)urea
• CAS: 3821-43-0
• 化学式: C₁₄H₁₁ClF₃N₃O₃S
• 分子量: 393.774
• InChiKey: GWCUTPKXYUYHMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  磺胺 、 4-氯-3-三氟甲基异氰酸苯酯 以60%的产率得到4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)benzenesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors based on sorafenib scaffold: Design, synthesis, crystallographic investigation and effects on primary breast cancer cells

  摘要：

  Carbonic anhydrase inhibitors (CAIs) of the sulfonamide, sulfamate and coumarin classes bearing the phenylureido tail found in the clinically used drug Sorafenib, a multikinase inhibitor actually used for the management of hepatocellular carcinomas, are reported. All compounds were assayed on human (h) CA isoforms I, II, VII and IX, involved in various pathologies. Among the sulfonamides, several compounds were selective for inhibiting hCA IX, with K-l values in the low nanomolar ranges (i.e. 0.7-30.2 nM). We explored the binding modes of such compounds by means of X-ray crystallographic studies on isoform hCA I in adduct with one sulfonamide and a sulfamate inhibitor. Antiproliferative properties of some sulfamates on breast tumor cell lines were also investigated. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111600

文献信息

• Carbonic anhydrase inhibitors based on sorafenib scaffold: Design, synthesis, crystallographic investigation and effects on primary breast cancer cells
  作者：Murat Bozdag、Marta Ferraroni、Carol Ward、Fabrizio Carta、Silvia Bua、Andrea Angeli、Simon P. Langdon、Ian H. Kunkler、Abdul-Malek S. Al-Tamimi、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2019.111600

  日期：2019.11

  Carbonic anhydrase inhibitors (CAIs) of the sulfonamide, sulfamate and coumarin classes bearing the phenylureido tail found in the clinically used drug Sorafenib, a multikinase inhibitor actually used for the management of hepatocellular carcinomas, are reported. All compounds were assayed on human (h) CA isoforms I, II, VII and IX, involved in various pathologies. Among the sulfonamides, several compounds were selective for inhibiting hCA IX, with K-l values in the low nanomolar ranges (i.e. 0.7-30.2 nM). We explored the binding modes of such compounds by means of X-ray crystallographic studies on isoform hCA I in adduct with one sulfonamide and a sulfamate inhibitor. Antiproliferative properties of some sulfamates on breast tumor cell lines were also investigated. (C) 2019 Elsevier Masson SAS. All rights reserved.