4-{4-[2'-(2-chloro-5-trifluoromethyl-phenoxymethyl)-biphenyl-4-yl]-[1,2,3]triazol-1-ylmethyl}-3-nitro-benzoic acid | 1394825-03-6

• 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-{4-[2'-(2-chloro-5-trifluoromethyl-phenoxymethyl)-biphenyl-4-yl]-[1,2,3]triazol-1-ylmethyl}-3-nitro-benzoic acid
• 英文别名: 4-[[4-[4-[2-[[2-Chloro-5-(trifluoromethyl)phenoxy]methyl]phenyl]phenyl]triazol-1-yl]methyl]-3-nitrobenzoic acid
• CAS: 1394825-03-6
• 化学式: C₃₀H₂₀ClF₃N₄O₅
• 分子量: 608.961
• InChiKey: IKSPEUQZRJJPPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-{4-[2'-(2-chloro-5-trifluoromethyl-phenoxymethyl)-biphenyl-4-yl]-[1,2,3]triazol-1-ylmethyl}-3-nitro-benzoic acid 在 tin(II) chloride dihdyrate 、 乙醇 作用下， 反应 0.5h， 以83%的产率得到3-Amino-4-[[4-[4-[2-[[2-chloro-5-(trifluoromethyl)phenoxy]methyl]phenyl]phenyl]triazol-1-yl]methyl]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-溴甲基-3-硝基苯甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium azide 、 铜 、 copper(II) sulfate 、 cesium fluoride 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 120.0 ℃ 、1.72 MPa 条件下， 反应 0.5h， 生成 4-{4-[2'-(2-chloro-5-trifluoromethyl-phenoxymethyl)-biphenyl-4-yl]-[1,2,3]triazol-1-ylmethyl}-3-nitro-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