ethyl 4-[({3-[amino(imino)methyl]phenyl}amino)methyl]-3-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate | 761392-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-[({3-[amino(imino)methyl]phenyl}amino)methyl]-3-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate
• 英文别名: Ethyl 4-[(3-carbamimidoylanilino)methyl]-3-[[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino]benzoate
• CAS: 761392-41-0
• 化学式: C₃₀H₃₆N₆O₃
• 分子量: 528.654
• InChiKey: CIYOLWMJTNGHDD-UHFFFAOYSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-[({3-[amino(imino)methyl]phenyl}amino)methyl]-3-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 4-((3-Carbamimidoylphenylamino)methyl)-3-(4-(4-methyl-1,4-diazepan-1-yl)benzamido)benzoic acid
  参考文献：
  名称：

  Synthesis and biological activity of novel 1,2-disubstituted benzene derivatives as factor Xa inhibitors

  摘要：

  Factor Xa (fXa) is a serine protease that plays a pivotal role in the coagulation cascade. High-tbroughput screening of the Yamanouchi compound library yielded lead compound I with the ability to inhibit fXa at micromolar concentrations. To improve its fXa inhibitory activity and its oral anticoagulant activity, the linker between benzamidine and the central benzene ring was modified and a carboxyl group was introduced at the central benzene ring. The resulting compounds 40b (YM-203552), 41a (YM-202054), and 41c (YM-203558) exhibited potent fXa inhibitory activity and oral anticoagulant activity. In particular, YM-203558 exhibited the most potent oral anticoagulant activity, prolonging PT more than 3-fold at 0.5 and 2.0h. Additionally, these compounds showed a high degree of selectivity for other serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.005
• 作为产物：
  描述：

  乙基 4-甲基-3-硝基苯甲酸 在 吡啶 、 乙酸铵 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 ammonium chloride 、 铁粉 、 potassium carbonate 作用下， 以 四氯化碳 、 乙醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 107.5h， 生成 ethyl 4-[({3-[amino(imino)methyl]phenyl}amino)methyl]-3-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzoate
  参考文献：
  名称：

  Synthesis and biological activity of novel 1,2-disubstituted benzene derivatives as factor Xa inhibitors

  摘要：

  Factor Xa (fXa) is a serine protease that plays a pivotal role in the coagulation cascade. High-tbroughput screening of the Yamanouchi compound library yielded lead compound I with the ability to inhibit fXa at micromolar concentrations. To improve its fXa inhibitory activity and its oral anticoagulant activity, the linker between benzamidine and the central benzene ring was modified and a carboxyl group was introduced at the central benzene ring. The resulting compounds 40b (YM-203552), 41a (YM-202054), and 41c (YM-203558) exhibited potent fXa inhibitory activity and oral anticoagulant activity. In particular, YM-203558 exhibited the most potent oral anticoagulant activity, prolonging PT more than 3-fold at 0.5 and 2.0h. Additionally, these compounds showed a high degree of selectivity for other serine proteases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.005