4-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid | 849752-96-1

• 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-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid
• 英文别名: 4-[2-[(Dimethylamino)methyl]imidazol-1-yl]benzoic acid
• CAS: 849752-96-1
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: LLYBHHDLRAFBJX-UHFFFAOYSA-N

物化性质

• 沸点：
  436.4±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid 、 (1R, 2S)-3-chloro-1H-indole-6-carboxylic acid (2-amino-cyclohexyl)-amide 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-chloro-N-((1R,2S)-2-(4-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)benzamido)cyclohexyl)-1H-indole-6-carboxamide
  参考文献：
  名称：

  SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa

  摘要：

  In the search of Factor Xa (FXa) inhibitors structurally different from the pyrazole-based series, we identified a viable series of enantiopure cis-(1R,2S)-cycloalkyldiamine derivatives as potent and selective inhibitors of FXa. Among them, cyclohexyldiamide 7 and cyclopentyldiamide 9 were the most potent neutral compounds, and had good anticoagulant activity comparable to the pyrazole-based analogs. Crystal structures of 7-FXa and 9-FXa illustrate binding similarities and differences between the five-and the six-membered core systems, and provide rationales for the observed SAR of PI and linker moieties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.029
• 作为产物：
  描述：

  2-[(二甲氨基)甲基]咪唑 在 sodium hydroxide 、 copper(l) iodide 、 1,10-菲罗啉 、 水 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 4-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid
  参考文献：
  名称：

  [EN] CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  [FR] DIAMINES CYCLIQUES ET DERIVES COMME INHIBITEURS DU FACTEUR XA

  摘要：

  公开号：

  WO2005032490A3

文献信息

• Cyclic diamines and derivatives as factor Xa inhibitors
  申请人：Qiao X. Jennifer

  公开号：US20050085511A1

  公开（公告）日：2005-04-21

  The present application describes cyclic diamino compounds, derivatives thereof, and pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

  本申请描述了环状二氨基化合物及其衍生物和药学上可接受的盐形式，其作为因子Xa的抑制剂是有用的。
• CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1670739A2

  公开（公告）日：2006-06-21
• EP1670739A4
  申请人：——

  公开号：EP1670739A4

  公开（公告）日：2007-08-08
• US7115646B2
  申请人：——

  公开号：US7115646B2

  公开（公告）日：2006-10-03
• SAR and X-ray structures of enantiopure 1,2-cis-(1R,2S)-cyclopentyldiamine and cyclohexyldiamine derivatives as inhibitors of coagulation Factor Xa
  作者：Jennifer X. Qiao、Chong-Hwan Chang、Daniel L. Cheney、Paul E. Morin、Gren Z. Wang、Sarah R. King、Tammy C. Wang、Alan R. Rendina、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler、Patrick Y.S. Lam

  DOI：10.1016/j.bmcl.2007.06.029

  日期：2007.8

  In the search of Factor Xa (FXa) inhibitors structurally different from the pyrazole-based series, we identified a viable series of enantiopure cis-(1R,2S)-cycloalkyldiamine derivatives as potent and selective inhibitors of FXa. Among them, cyclohexyldiamide 7 and cyclopentyldiamide 9 were the most potent neutral compounds, and had good anticoagulant activity comparable to the pyrazole-based analogs. Crystal structures of 7-FXa and 9-FXa illustrate binding similarities and differences between the five-and the six-membered core systems, and provide rationales for the observed SAR of PI and linker moieties. (c) 2007 Elsevier Ltd. All rights reserved.