(1S,3S,2'S)-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)amino>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline | 170300-08-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S,2'S)-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)amino>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
• 英文别名: methyl (1S,3S)-1-[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 170300-08-0
• 化学式: C₃₁H₃₁N₃O₆
• 分子量: 541.604
• InChiKey: DRCPRXMOMMNXAR-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  118.75
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,2'S)-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 xylene 为溶剂， 反应 24.0h， 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
• 作为产物：
  描述：

  (S)-1-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 以 xylene 为溶剂， 反应 24.0h， 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 、 (1S,3S,2'S)-1-<2'-benzyloxycarbonyl-2'-(benzyloxycarbonyl)amino>ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
  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.