5-(Aminomethyl)-1,2,4-oxadiazole-3-carbonitrile | 758668-26-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(Aminomethyl)-1,2,4-oxadiazole-3-carbonitrile
• CAS: 758668-26-7
• 化学式: C₄H₄N₄O
• mdl: MFCD19214552
• 分子量: 124.102
• InChiKey: CDRKTTOGZXVYNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(Aminomethyl)-1,2,4-oxadiazole-3-carbonitrile 、 (S)-1-[(R)-2-(tert-Butoxycarbonyl-tert-butoxycarbonylmethyl-amino)-3-cyclohexyl-propionyl]-2,5-dihydro-1H-pyrrole-2-carboxylic acid 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Orally active thrombin inhibitors. Part 1: Optimization of the P1-moiety

  摘要：

  The synthesis and SAR of novel nanomolar thrombin inhibitors with the common backbone HOOC-CH2-D-cyclohexylalanyl-3,.4-dehydroprolyl-NH-CH2-aryl-C(=NH)NH2 are described together with their ecarin clotting time (ECT) prolongation as measure for thrombin inhibition ex vivo. The aryl P1-moiety mimicking the arginine part of the D-Phe-Pro-Arg derived thrombin inhibitors turned out to be a key component for in vitro potency and in vivo activity. Optimization of this part led to compounds with improved antithrombin activity in rats and dogs after oral administration compared to the recently launched anticoagulant melagatran. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.040

文献信息

• Orally active thrombin inhibitors. Part 1: Optimization of the P1-moiety
  作者：Helmut Mack、Dorit Baucke、Wilfried Hornberger、Udo E.W. Lange、Werner Seitz、H. Wolfgang Höffken

  DOI：10.1016/j.bmcl.2006.02.040

  日期：2006.5

  The synthesis and SAR of novel nanomolar thrombin inhibitors with the common backbone HOOC-CH2-D-cyclohexylalanyl-3,.4-dehydroprolyl-NH-CH2-aryl-C(=NH)NH2 are described together with their ecarin clotting time (ECT) prolongation as measure for thrombin inhibition ex vivo. The aryl P1-moiety mimicking the arginine part of the D-Phe-Pro-Arg derived thrombin inhibitors turned out to be a key component for in vitro potency and in vivo activity. Optimization of this part led to compounds with improved antithrombin activity in rats and dogs after oral administration compared to the recently launched anticoagulant melagatran. (C) 2006 Elsevier Ltd. All rights reserved.