3-({2-[(4-{amino-[(E)-pentyloxycarbonylimino]methyl}-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid-{3-methoxy-4-[(E)-2-methoxycarbonylvinyl]phenyl}ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-({2-[(4-{amino-[(E)-pentyloxycarbonylimino]methyl}-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid-{3-methoxy-4-[(E)-2-methoxycarbonylvinyl]phenyl}ester
• 英文别名: [3-methoxy-4-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl] 3-[[1-methyl-2-[[4-[(Z)-N'-pentoxycarbonylcarbamimidoyl]anilino]methyl]benzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
• 化学式: C₄₂H₄₅N₇O₈
• 分子量: 775.861
• InChiKey: VMWBUVMQNBPJKH-HMMYKYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  氯甲酸正戊酯 在 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 3-({2-[(4-{amino-[(E)-pentyloxycarbonylimino]methyl}-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid-{3-methoxy-4-[(E)-2-methoxycarbonylvinyl]phenyl}ester
  参考文献：
  名称：

  Design, synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing methyl ferulate

  摘要：

  A novel series of prodrugs containing dabigatran and methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate (methyl ferulate) were synthesized. All of them reveal the effect of thrombin-induced antiplatelet aggregation in vitro. In addition, in vivo experiment shows that one of the target compounds, X-2 (ED50 = 3.7 +/- 1.0 mu mol/kg) possesses a more potent activity for inhibiting venous thrombosis than that of dabigatran etexilate (ED50 = 7.8 +/- 1.5 mu mol/kg). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.126

文献信息

• Design, synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing methyl ferulate
  作者：Xiao-Zhi Yang、Xiao-Juan Diao、Wen-Hui Yang、Feng Li、Guang-Wei He、Guo-Qing Gong、Yun-Gen Xu

  DOI：10.1016/j.bmcl.2013.01.126

  日期：2013.4

  A novel series of prodrugs containing dabigatran and methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate (methyl ferulate) were synthesized. All of them reveal the effect of thrombin-induced antiplatelet aggregation in vitro. In addition, in vivo experiment shows that one of the target compounds, X-2 (ED50 = 3.7 +/- 1.0 mu mol/kg) possesses a more potent activity for inhibiting venous thrombosis than that of dabigatran etexilate (ED50 = 7.8 +/- 1.5 mu mol/kg). (C) 2013 Elsevier Ltd. All rights reserved.