(2R,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole | 342648-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
• 英文别名: methyl (2R,5S,11bR)-3-oxo-2-(phenylmethoxycarbonylamino)-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indole-5-carboxylate
• CAS: 342648-00-4
• 化学式: C₂₄H₂₃N₃O₅
• 分子量: 433.464
• InChiKey: HANVNUZDIXCWDB-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (2R,5S,11bR)-2-Amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Conformationally constrained analogues of endogenous tripeptide inhibitors of zinc metalloproteinases

  摘要：

  Two diastereomeric furan-2-carbonylamino-3-oxohexahydroindolizino[8,7-b]indole carboxylates, highly constrained analogues of endogenous pyroglutamyl tripeptide inhibitors of snake venom endopeptidases, have been prepared as potential inhibitors of adamalysin II and matrix metalloproteinases. They proved to be inactive against adamalysin II and weak inhibitors of gelatinase A, gelatinase B, stromelysin 1 and human neutrophyl collagenase. Evaluation of the mode of binding of the (2R,5S,11bR) isomer in the active site of adamalysin II suggests that the decrease of potency may be due to the reorientation of the acylamino chain in three of the heterocyclic nucleus, to a short contact at the entrance of the S-1' hydrophobic cleft and to the loss of flexibility of the tetracyclic nucleus in the P-1', P-2' region of the inhibitor, which prevents optimal arrangement in the S-1' specificity subsite. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01192-2
• 作为产物：
  描述：

  (3S,2'R)-1-[2-benzyloxycarbonyl-2-(benzyloxycarbonyl)amino]ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以1.977 g的产率得到(2R,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
  参考文献：
  名称：

  Conformationally constrained analogues of endogenous tripeptide inhibitors of zinc metalloproteinases

  摘要：

  Two diastereomeric furan-2-carbonylamino-3-oxohexahydroindolizino[8,7-b]indole carboxylates, highly constrained analogues of endogenous pyroglutamyl tripeptide inhibitors of snake venom endopeptidases, have been prepared as potential inhibitors of adamalysin II and matrix metalloproteinases. They proved to be inactive against adamalysin II and weak inhibitors of gelatinase A, gelatinase B, stromelysin 1 and human neutrophyl collagenase. Evaluation of the mode of binding of the (2R,5S,11bR) isomer in the active site of adamalysin II suggests that the decrease of potency may be due to the reorientation of the acylamino chain in three of the heterocyclic nucleus, to a short contact at the entrance of the S-1' hydrophobic cleft and to the loss of flexibility of the tetracyclic nucleus in the P-1', P-2' region of the inhibitor, which prevents optimal arrangement in the S-1' specificity subsite. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01192-2