methyl 3-fluoro-4-[(1R)-1-[[1-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]cyclopropanecarbonyl]amino]ethyl]benzoate | 1134776-74-1

• 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: methyl 3-fluoro-4-[(1R)-1-[[1-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]cyclopropanecarbonyl]amino]ethyl]benzoate
• CAS: 1134776-74-1
• 化学式: C₂₂H₁₉F₅N₂O₄
• 分子量: 470.396
• InChiKey: RDAZYZQCBSDVKK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3-fluoro-4-[(1R)-1-[[1-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]cyclopropanecarbonyl]amino]ethyl]benzoate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-fluoro-4-[(1R)-1-[[1-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]cyclopropanecarbonyl]amino]ethyl]benzoic acid
  参考文献：
  名称：

  Novel small molecule bradykinin B1 receptor antagonists. Part 1: Benzamides and semicarbazides

  摘要：

  The synthesis and SAR of two series of bradykinin B-1 receptor antagonists is described. The benzamide moiety proved to be a suitable replacement for the aryl ester functionality of biaryl based antagonists. In addition, it was found that semicarbazides can effectively replace cyclopropyl amino acids. The compounds with the best overall pro. le were biaryl semicarbazides which display high antagonistic activity, low Caco-2 efflux and high oral bioavailability in the rat. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.119
• 作为产物：
  描述：

  、 3-氟-5-(三氟甲基)苯甲酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 3-fluoro-4-[(1R)-1-[[1-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]cyclopropanecarbonyl]amino]ethyl]benzoate
  参考文献：
  名称：

  Novel small molecule bradykinin B1 receptor antagonists. Part 1: Benzamides and semicarbazides

  摘要：

  The synthesis and SAR of two series of bradykinin B-1 receptor antagonists is described. The benzamide moiety proved to be a suitable replacement for the aryl ester functionality of biaryl based antagonists. In addition, it was found that semicarbazides can effectively replace cyclopropyl amino acids. The compounds with the best overall pro. le were biaryl semicarbazides which display high antagonistic activity, low Caco-2 efflux and high oral bioavailability in the rat. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.119

文献信息

• SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS
  申请人：Jerini AG

  公开号：EP2195288A2

  公开（公告）日：2010-06-16
• [EN] SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTE DE FAIBLE MASSE MOLÉCULAIRE DU RÉCEPTEUR B1 DE LA BRADYKININE
  申请人：JERINI AG

  公开号：WO2009036996A2

  公开（公告）日：2009-03-26

  Disclosed are compounds of formula (I) which are bradykinin B1 receptor (B1R) antagonists. These compounds are useful to treat diseases or relieve adverse symptoms associated with inflammation and pain. The invention encompasses novel compounds and acceptable derivatives thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases involving inflammation and pain.