2,4-dichloro-5-[5-(4-chlorophenyl)-1,2,4-triazol-3-yl]benzenesulfonamide | 1617508-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-dichloro-5-[5-(4-chlorophenyl)-1,2,4-triazol-3-yl]benzenesulfonamide
• 英文别名: 2,4-dichloro-5-[3-(4-chlorophenyl)-1H-1,2,4-triazol-5-yl]benzenesulfonamide
• CAS: 1617508-83-4
• 化学式: C₁₄H₉Cl₃N₄O₂S
• 分子量: 403.676
• InChiKey: AYFNVXHJZPBGPG-UHFFFAOYSA-N

物化性质

• 熔点：
  288-290 °C
• 沸点：
  663.877±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.617±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二氯-5-磺酰胺基苯甲酸 在 氯化亚砜 、 hydrazine hydrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 氘代甲醇-d 为溶剂， 反应 9.0h， 生成 2,4-dichloro-5-[5-(4-chlorophenyl)-1,2,4-triazol-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis of a novel series of 5-substituted 2,4-dichlorobenzenesulfonamides and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII

  摘要：

  A series of novel 5-substituted 2,4-dichlorobenzenesulfonamides 5a-c, 6a-d, 7a-j and 10a-i have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and tumor-associated isozymes CA IX and XII. Against the human CA I investigated compounds displayed K-I values from 349 to 7355 nM, toward hCA II at range of 6.9 to 164 nM, while against hCA IX ranging from 2.8 to 76 nM and against hCA XII in the range of 2.7 to 95 nM. The excellent inhibitory activity against tumor-associated hCA IX was found. The twenty one new compounds displayed a powerful inhibitory potency toward hCA IX (K-I = 2.8-21.7 nM) in comparison with the clinically used CAIs AAZ, MZA, EZA, DCP and IND (24-50 nM). Among them the most potent hCA IX inhibitor 7b (K-I = 2.8 nM) was 8.5-fold stronger than IND (K-I = 24 nM). Toward tumor-associated hCA XII compounds 6c and 10a (K-I = 2.7 and 2.8 nM, respectively) showed a better inhibitory potency than reference sulfonamides MZA and IND (K-I = 3.4 nM). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.039