(E)-5-[(E)-3-(4-Carboxy-phenyl)-2-methyl-acryloylamino]-5-ethoxycarbonyl-hex-2-enedioic acid diethyl ester | 192637-02-8

• 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: (E)-5-[(E)-3-(4-Carboxy-phenyl)-2-methyl-acryloylamino]-5-ethoxycarbonyl-hex-2-enedioic acid diethyl ester
• CAS: 192637-02-8
• 化学式: C₂₄H₂₉NO₉
• 分子量: 475.496
• InChiKey: QLTYDJKYFHVDGW-IZCPETMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  145.3
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-羟基苯甲脒盐酸盐 、 (E)-5-[(E)-3-(4-Carboxy-phenyl)-2-methyl-acryloylamino]-5-ethoxycarbonyl-hex-2-enedioic acid diethyl ester 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 15.0h， 以53%的产率得到triethyl (E)-1-[[(E)-3-[4-(4-carbamimidoylphenoxy)carbonylphenyl]-2-methylprop-2-enoyl]amino]but-3-ene-1,1,4-tricarboxylate
  参考文献：
  名称：

  New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity

  摘要：

  A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00036-9
• 作为产物：
  描述：

  二乙基(Boc-氨基)乙酯 在 盐酸 、 4-二甲氨基吡啶 、 2-氯-1-甲基吡啶碘化物 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.5h， 生成 (E)-5-[(E)-3-(4-Carboxy-phenyl)-2-methyl-acryloylamino]-5-ethoxycarbonyl-hex-2-enedioic acid diethyl ester
  参考文献：
  名称：

  New serine protease inhibitors with leukotriene B4 (LTB4) receptor binding affinity

  摘要：

  A series of new trypsin-like serine protease inhibitors, 1, 2 and 7-23, containing amidinobenzene moiety was found to show potent LTB4-receptor affinity. Among them, compounds 1 and 2 were found to be LTB4 receptor antagonists based on an inhibition assay of human polymorphonuclear neutrophil (PMN) intracellular calcium mobilization induced by LTB4. Compounds 1 and 2, which satisfy the reported structural requirements for good oral activity, are expected to show a balanced dual mode of action, i.e., protease inhibitory activity and LTB4 receptor antagonist activity, in vivo. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00036-9