(R)-4-[1-({1-[(pyrimidine-5-carbonyl)amino]cyclopropanecarbonyl}amino)ethyl]benzoic acid | 1134777-42-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-4-[1-({1-[(pyrimidine-5-carbonyl)amino]cyclopropanecarbonyl}amino)ethyl]benzoic acid
• 英文别名: 4-[(1R)-1-[[1-(pyrimidine-5-carbonylamino)cyclopropanecarbonyl]amino]ethyl]benzoic acid
• CAS: 1134777-42-6
• 化学式: C₁₈H₁₈N₄O₄
• 分子量: 354.365
• InChiKey: RHHLUJBYOBHPHP-LLVKDONJSA-N

物化性质

• 沸点：
  738.9±60.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-[1-({1-[(pyrimidine-5-carbonyl)amino]cyclopropanecarbonyl}amino)ethyl]benzoic acid 、 乙胺 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 (R)-N-(1-(1-(4-(ethylcarbamoyl)phenyl)ethylcarbamoyl)cyclopropyl)pyrimidine-5-carboxamide
  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：

  (R)-4-[1-({1-[(pyrimidine-5-carbonyl)amino]cyclopropanecarbonyl}amino)ethyl]benzoic acid methyl ester 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 (R)-4-[1-({1-[(pyrimidine-5-carbonyl)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

文献信息

• Novel small molecule bradykinin B1 receptor antagonists. Part 1: Benzamides and semicarbazides
  作者：Marco Schaudt、Elsa Locardi、Gunther Zischinsky、Roland Stragies、Jochen R. Pfeifer、Christoph Gibson、Dirk Scharn、Uwe Richter、Holger Kalkhof、Klaus Dinkel、Karsten Schnatbaum

  DOI：10.1016/j.bmcl.2009.11.119

  日期：2010.2

  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.