(2S,5S,11bR)-2-(tert-butoxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino-<8,7-b>indole | 170552-58-6

• 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-(tert-butoxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino-<8,7-b>indole
• 英文别名: (2S,5S,11bR)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indole-5-carboxylic acid
• CAS: 170552-58-6
• 化学式: C₂₀H₂₃N₃O₅
• 分子量: 385.42
• InChiKey: IKYIUGNSUOYTRE-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  111.73
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,5S,11bR)-2-(tert-butoxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino-<8,7-b>indole 在 sodium hydroxide 、 TEA 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 (R)-3-[((2S,5S,11bR)-2-tert-Butoxycarbonylamino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-4-phenyl-butyric acid
  参考文献：
  名称：

  Highly constrained dipeptoid analogues containing a type II′ β-turn mimic as novel and selective CCK-A receptor ligands

  摘要：

  Conformationally constrained dipeptoid analogues containing the type II' beta-turn mimic (2S,5S,11bR)-2-amino-3-oxohexahydroindolizino[8,7-b] indoled-carboxylate framework in place of the alpha-MeTrp residue, show high binding affinity and selectivity for CCK-A receptors, suggesting that a turn-like conformation could contribute to the bioactive conformation at this CCK receptor subtype. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00677-5
• 作为产物：
  描述：

  (2S,5S,11bR)-2-(tert-butoxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino<8,7-b>indole 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到(2S,5S,11bR)-2-(tert-butoxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino-<8,7-b>indole
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/0040-4020(95)00402-t