(2S,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole | 170552-54-2

• 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: (2S,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: (2S,5S,11bR)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole；methyl (2S,5S,11bR)-3-oxo-2-(phenylmethoxycarbonylamino)-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indole-5-carboxylate
• CAS: 170552-54-2
• 化学式: C₂₄H₂₃N₃O₅
• 分子量: 433.464
• InChiKey: HANVNUZDIXCWDB-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  100.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,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 sodium hydroxide 、 甲酸铵 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (2S,5S,11bR)-2-[(Furan-2-carbonyl)-amino]-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid
  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：

  (2S,5S,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole 在 三氟乙酸 作用下， 以 xylene 为溶剂， 生成 (2S,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：

  2(S)-amino-3-oxo-11b(R)-hexahydroindolizino[8,7-b]indole-5(S)-carboxylate as a new type of β-turn dipeptide mimetic

  摘要：

  Molecular-modelling studies have shown that 2(S)-amino-3-oxo-11 b(R)-hexahydroindolizino[8,7-b]indole-5(S)-carboxylate, stereoselectively prepared by Pictet-Spengler reaction between H-Trp-OMe and Z-Asp(H)-OBz and subsequent gamma-lactamization, behaves as a type-ll' beta-turn inducing mimetic.

  DOI：

  10.1039/c39940000613

文献信息

• 2-Amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate derivatives as new scaffolds for mimicking β-turn secondary structures. Molecular dynamics and stereoselective synthesis
  作者：Natalia De la Figuera、Ibon Alkorta、M. Teresa García-López、Rosario Herranz、Rosario González-Muñiz

  DOI：10.1016/0040-4020(95)00402-t

  日期：1995.7

  Highly constrained 2-amino-3-oxohexahydroindolizino[8-7-b]indole-5-carboxylate derivatives of general formula 1 have been developed as novel beta-turn mimetics. Molecular dynamics studies on model structures 2a and 2b have revealed that both indolizinoindole derivatives are able to adopt conformations close to those of ideal type II' beta-turn. The asymmetric synthesis of this heterocyclic system was accomplished from 1,3-di- and 1,2,3-trisubstituted tetrahydro-beta-carbolines, which were prepared in stereoselective or stereospecific way by application of the Pictet-Spengler reaction.