3-benzyl-6-oxo-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-2-carboxylic acid methyl ester | 60702-98-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吲哚萘啶生物碱
• 英文名称: 3-benzyl-6-oxo-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-2-carboxylic acid methyl ester
• 英文别名: Methyl-1,2,3,3a,4,5-hexahydro-6-oxocanthin-2-carboxylat；Methyl 6-benzyl-2-oxo-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-9(16),10,12,14-tetraene-7-carboxylate
• CAS: 60702-98-9
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: HIZDIZAXVJCWFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-6-oxo-2,3,3a,4,5,6-hexahydro-1H-indolo[3,2,1-de][1,5]naphthyridine-2-carboxylic acid methyl ester 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以66%的产率得到2-(methoxycarbonyl)canthin-6-one
  参考文献：
  名称：

  Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids

  摘要：

  DOI：

  10.1021/ja00342a045
• 作为产物：
  描述：

  N_b-benzyltriptophan methyl ester 以50%的产率得到
  参考文献：
  名称：

  SANDRIN J.; SOERENS D.; HUTCHINS L.; RICHFIELD E.; UNGEMACH F.; COOK J. M+, HETEROCYCLES, 1976, 4, NO 6, 1101-1105

  摘要：

  DOI：

文献信息

• Biomimetic approach to potential benzodiazepine receptor agonists and antagonists
  作者：Filadelfo Guzman、Michael Cain、Paul Larscheid、Tim Hagen、James M. Cook、Margaret Schweri、Phil Skolnick、Steven M. Paul

  DOI：10.1021/jm00371a002

  日期：1984.5

  Several beta-carbolines, isoquinolines, imidazopyridines , and canthin -6-ones prepared in biomimetic fashion were tested for their ability to bind to the benzodiazepine receptor. Methyl isoquinoline-3-carboxylate, methyl 6,7- dimethoxyisoquinoline -3-carboxylate (3b) 1-phenyl-3- carbomethoxyimidazopyridine , (6B,) and canthin -6- one ( 13a ) bound with moderate affinities, while 2- carbomethoxycanthin -6- one ( 13b ) bound to benzodiazepine receptors with an affinity comparable to several pharmacologically active benzodiazepines. The potency of 13b suggests that the benzodiazepine receptor(s) can tolerate substitution at positions 1 and 9 of a beta-carboline without loss of activity if the substituents are trigonal and maintain a planar topography. Moreover, displacement of the carbonyl group by two atoms from the aromatic ring (C) of the beta-carboline skeleton caused a marked decrease in binding to the benzodiazepine receptor. This observation supports the hypothesis that maximum binding affinity of beta-carbolines is achieved when the carbonyl group at position 3 is attached directly to the aromatic pyridine ring.