4-[4-[3-(trifluoromethyl)phenyl-1,3,4-thiadoazol-2-yl]amino]benzoic acid | 1073613-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-[3-(trifluoromethyl)phenyl-1,3,4-thiadoazol-2-yl]amino]benzoic acid
• 英文别名: 4-{4-[3-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl}benzoic acid；4-[4-(3-Trifluoromethyl-phenyl)-[1,2,3]triazol-1-yl]-benzoic acid；4-[4-[3-(trifluoromethyl)phenyl]triazol-1-yl]benzoic acid
• CAS: 1073613-05-4
• 化学式: C₁₆H₁₀F₃N₃O₂
• 分子量: 333.27
• InChiKey: AGOZGNSQFLJGFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对叠氮苯甲酸 、 3-乙炔基-α,α,α-三氟甲苯 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以92%的产率得到4-[4-[3-(trifluoromethyl)phenyl-1,3,4-thiadoazol-2-yl]amino]benzoic acid
  参考文献：
  名称：

  WATER SOLUBLE SMALL MOLECULE INHIBITORS OF THE CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

  摘要：

  本文提供了高度水溶性的噻唑啉酮衍生物化合物和甘氨酸酰肼衍生物化合物，这些化合物抑制了囊性纤维化跨膜传导调节器（CFTR）的离子传输活性。本文描述的化合物和含有这些化合物的组合物对于治疗与CFTR活性异常增加相关的疾病、紊乱和疾病、紊乱和条件的后遗症非常有用，例如分泌性腹泻。这些化合物也可用于抑制或预防多囊肾病患者囊肿的扩张或形成。

  公开号：

  US20110105565A1

文献信息

• Thiazolidinone CFTR inhibitors with improved water solubility identified by structure–activity analysis
  作者：N.D. Sonawane、A.S. Verkman

  DOI：10.1016/j.bmc.2008.07.044

  日期：2008.9

  The thiazolidinone 3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone (CFTRinh-172) inhibits cystic fibrosis transmembrane conductance regulator ( CFTR) chloride channel conductance with submicromolar affinity and blocks cholera toxin-induced intestinal fluid secretion. Fifty-eight CFTRinh-172 analogs were synthesized to identify CFTR inhibitors with improved water solubility, exploring modi. cations in its two phenyl rings, thiazolidinone core, and core-phenyl connectors. Greatest CFTR inhibition potency was found for 3-CF3 and polar group-substituted-phenyl rings, and a thiazolidinone core. Two compounds with similar to 1 mu M CFTR inhibition potency and solubility >180 mu M(>10-fold more than CFTRinh-172) were identified: Tetrazolo-172, containing 4-tetrazolophenyl in place of 4-carboxyphenyl, and Oxo-172, containing thiazolidinedione in place of the thiazolidinone core. These water soluble thiazolidinone analogs had low cellular toxicity. The improved water solubility of Tetrazolo- and Oxo-172 make them potential lead candidates for therapy of secretory diarrheas and polycystic kidney disease. (C) 2008 Elsevier Ltd. All rights reserved.