6-benzylamino-β-carboline-3-carboxylic acid methyl ester | 107081-75-4

• 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: 6-benzylamino-β-carboline-3-carboxylic acid methyl ester
• 英文别名: 6-benzylamino-3-methoxycarbonyl-β-carboline；6-Benzylamino-9H-beta-carboline-3-carboxylic acid methyl ester；methyl 6-(benzylamino)-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 107081-75-4
• 化学式: C₂₀H₁₇N₃O₂
• 分子量: 331.374
• InChiKey: JTYYMOMTGZSRFM-UHFFFAOYSA-N

物化性质

• 熔点：
  206-270.25 °C
• 沸点：
  596.3±45.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzylamino-β-carboline-3-carboxylic acid methyl ester 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 6-(benzylamino)-3-(hydroxymethyl)-β-carboline
  参考文献：
  名称：

  Synthesis of 6-substituted .beta.-carbolines that behave as benzodiazepine receptor antagonists or inverse agonists

  摘要：

  The synthesis of the first beta-carboline, 6-(benzylamino)-beta-carboline (1c), to be devoid of a substituent at the 3-position and that still binds to benzodiazepine receptors with potent affinity is described. Furthermore, 1c proved to be a partial inverse agonist when tested in mice. Addition of the benzylamino group at the 6-position of the beta-carboline nucleus is primarily responsible for the activity of beta-carbolines 1b and 1c. The importance of the Nb-nitrogen atom for binding affinity was also demonstrated since 3-(benzylamino)carbazole (6) exhibited little or no affinity for benzodiazepine receptors in vitro, in contrast to the activity of 1c.

  DOI：

  10.1021/jm00387a033
• 作为产物：
  描述：

  2,3,4,9-四氢-1H-beta-咔啉-3-甲酸 在 palladium on activated charcoal 盐酸 、 氢气 、 硝酸 、 sodium cyanoborohydride 、 sulfur 、 溶剂黄146 作用下， 以 甲醇 、 xylene 为溶剂， 反应 8.5h， 生成 6-benzylamino-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Hagen, Timothy J.; Guzman, Filadelfo; Schultz, Christopher, Heterocycles, 1986, vol. 24, # 10, p. 2845 - 2855

  摘要：

  DOI：

文献信息

• HAGEN T. J.; SKOLNICK PH.; COOK J. M., J. MED. CHEM., 30,(1987) N 4, 750-753
  作者：HAGEN T. J.、 SKOLNICK PH.、 COOK J. M.

  DOI：——

  日期：——
• Hagen, Timothy J.; Guzman, Filadelfo; Schultz, Christopher, Heterocycles, 1986, vol. 24, # 10, p. 2845 - 2855
  作者：Hagen, Timothy J.、Guzman, Filadelfo、Schultz, Christopher、Cook, James M.、Skolnick, Phil、Shannon, Harlan E.

  DOI：——

  日期：——
• Synthesis of 6-substituted .beta.-carbolines that behave as benzodiazepine receptor antagonists or inverse agonists
  作者：Timothy J. Hagen、Phil Skolnick、James M. Cook

  DOI：10.1021/jm00387a033

  日期：1987.4

  The synthesis of the first beta-carboline, 6-(benzylamino)-beta-carboline (1c), to be devoid of a substituent at the 3-position and that still binds to benzodiazepine receptors with potent affinity is described. Furthermore, 1c proved to be a partial inverse agonist when tested in mice. Addition of the benzylamino group at the 6-position of the beta-carboline nucleus is primarily responsible for the activity of beta-carbolines 1b and 1c. The importance of the Nb-nitrogen atom for binding affinity was also demonstrated since 3-(benzylamino)carbazole (6) exhibited little or no affinity for benzodiazepine receptors in vitro, in contrast to the activity of 1c.