(2E)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-3-(1-propyl-1H-imidazol-4-yl)-2-propenoic acid | 400046-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2E)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-3-(1-propyl-1H-imidazol-4-yl)-2-propenoic acid
• 英文别名: 2-(3-tert-butoxycarbonylaminopropyl-3-(1-n-propyl-1H-imidazol-4-yl)acrylic acid；(2E)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(1-propylimidazol-4-yl)methylidene]pentanoic acid
• CAS: 400046-11-9
• 化学式: C₁₇H₂₇N₃O₄
• 分子量: 337.419
• InChiKey: QJHHZSHQPWRYCL-JLHYYAGUSA-N

物化性质

• 沸点：
  578.4±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-3-(1-propyl-1H-imidazol-4-yl)-2-propenoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、413.68 kPa 条件下， 反应 18.0h， 以96%的产率得到5-[(tert-butoxycarbonyl)amino]-2-(1-propyl-1H-imidazol-4-ylmethyl)pentanoic acid
  参考文献：
  名称：

  Efficient Synthesis of an Imidazole-Substituted δ-Amino Acid by the Integration of Chiral Technologies

  摘要：

  [GRAPHICS]Two methods to produce (2S)-5-amino-2-(1-n-propyl-1H-imidazol-4-ylmethyl)-pentanoic acid were investigated. Diastereoisomeric salt resolution, using the quinidine salt, gave the desired intermediate in 98% ee and 33% yield. Asymmetric hydrogenation of various substrates gave high conversions, with up to 83% ee. Integration of these two approaches via asymmetric hydrogenation of a quinidine salt substrate followed by crystallization provided the desired intermediate in 94% ee and 76% yield.

  DOI：

  10.1021/ol0503081
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (2E)-2-{3-[(tert-butoxycarbonyl)amino]propyl}-3-(1-propyl-1H-imidazol-4-yl)-2-propenoic acid
  参考文献：
  名称：

  Efficient Synthesis of an Imidazole-Substituted δ-Amino Acid by the Integration of Chiral Technologies

  摘要：

  [GRAPHICS]Two methods to produce (2S)-5-amino-2-(1-n-propyl-1H-imidazol-4-ylmethyl)-pentanoic acid were investigated. Diastereoisomeric salt resolution, using the quinidine salt, gave the desired intermediate in 98% ee and 33% yield. Asymmetric hydrogenation of various substrates gave high conversions, with up to 83% ee. Integration of these two approaches via asymmetric hydrogenation of a quinidine salt substrate followed by crystallization provided the desired intermediate in 94% ee and 76% yield.

  DOI：

  10.1021/ol0503081

文献信息

• Pharmaceuticals
  申请人：——

  公开号：US20020147229A1

  公开（公告）日：2002-10-10

  The present invention provides compounds of formula (I) 1 as well as the use of such compounds in pharmaceutical compositions and methods of treatment. The compounds described herein represent a class of TAFIla inhibitors suitable for use in treating conditions such as thrombosis, atherosclerosis, adhesions, dermal scarring, cancer, fibrotic conditions, inflammatory diseases and those conditions which benefit from maintaining or enhancing bradykinin levels in the body.

  本发明提供了式(I)1的化合物，以及这些化合物在制药组合物和治疗方法中的应用。本文描述的化合物代表了一类适用于治疗血栓形成、动脉粥样硬化、粘连、皮肤瘢痕、癌症、纤维化疾病、炎症性疾病以及那些受益于维持或增强体内激肽酶激活因子Ⅰ（TAFIla）抑制剂的疾病的化合物。
• SUBSTITUTED IMIDAZOLES AS TAFIA INHIBITORS
  申请人：Pfizer Limited

  公开号：EP1311488B1

  公开（公告）日：2009-11-04
• US6949577B2
  申请人：——

  公开号：US6949577B2

  公开（公告）日：2005-09-27