3-(benzylamino)carbazole | 101868-79-5

• 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: 3-(benzylamino)carbazole
• 英文别名: N-benzyl-9H-carbazol-3-amine
• CAS: 101868-79-5
• 化学式: C₁₉H₁₆N₂
• 分子量: 272.349
• InChiKey: LFIMITGQRZRBBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(benzylamino)carbazole 、 盐酸 、 甲醇 生成 N-benzyl-9H-carbazol-3-amine;hydrochloride
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(9H-carbazol-3-yl)-1-phenylmethanimine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 3-(benzylamino)carbazole
  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

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：——
• 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.