4-[4-(4-bromo-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid | 1394825-11-6

• 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-(4-bromo-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid
• 英文别名: 4-{[4-(4-bromophenyl)-1H-1,2,3-triazol-1-yl]methyl}benzoic acid；4-[[4-(4-Bromophenyl)triazol-1-yl]methyl]benzoic acid；4-[[4-(4-bromophenyl)triazol-1-yl]methyl]benzoic acid
• CAS: 1394825-11-6
• 化学式: C₁₆H₁₂BrN₃O₂
• 分子量: 358.194
• InChiKey: JJEDYVCOIJHXEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-((2’-氯-5’-(三氟甲基)苯氧基)甲基)苯基硼酸 、 4-[4-(4-bromo-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 cesium fluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 120.0 ℃ 、1.72 MPa 条件下， 以65%的产率得到4-{4-[2'-(2-chloro-5-trifluoromethyl-phenoxymethyl)-biphenyl-4-yl]-[1,2,3]triazol-1-ylmethyl}-benzoic acid
  参考文献：
  名称：

  Design and synthesis of a second series of triazole-based compounds as potent dual mPGES-1 and 5-lipoxygenase inhibitors

  摘要：

  Microsomal prostaglandin E-2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO) are pivotal enzymes in the biosynthesis of the pro-inflammatory PGE(2) and leukotrienes, respectively. The design and synthesis of a second series of mPGES-1 inhibitors based on a triazole scaffold are described. Our studies allowed us to draw a tentative SAR profile and to optimize this series with the identification of compounds 10, 11 and 14-15 which displayed potent mPGES-1 inhibition in a cell-free assay. In addition, compounds 5, 10, 12 and 14-16 also blocked 5-LO activity in cell-free and cell-based test systems, emerging as very promising candidates for the development of safer and more effective anti-inflammatory drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.014
• 作为产物：
  描述：

  (4-溴苯基)乙炔 、 对溴甲基苯甲酸 在 sodium azide 、 铜 、 copper(II) sulfate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.5h， 以76%的产率得到4-[4-(4-bromo-phenyl)-[1,2,3]triazol-1-ylmethyl]-benzoic acid
  参考文献：
  名称：

  Design and synthesis of a second series of triazole-based compounds as potent dual mPGES-1 and 5-lipoxygenase inhibitors

  摘要：

  Microsomal prostaglandin E-2 synthase (mPGES)-1 and 5-lipoxygenase (5-LO) are pivotal enzymes in the biosynthesis of the pro-inflammatory PGE(2) and leukotrienes, respectively. The design and synthesis of a second series of mPGES-1 inhibitors based on a triazole scaffold are described. Our studies allowed us to draw a tentative SAR profile and to optimize this series with the identification of compounds 10, 11 and 14-15 which displayed potent mPGES-1 inhibition in a cell-free assay. In addition, compounds 5, 10, 12 and 14-16 also blocked 5-LO activity in cell-free and cell-based test systems, emerging as very promising candidates for the development of safer and more effective anti-inflammatory drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.014