1-methyl-4,5-dihydro-1H-benzoindole-3-carboxylic acid | 224558-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-4,5-dihydro-1H-benzoindole-3-carboxylic acid
• CAS: 224558-97-8
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: UQOHLZGUJIUGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-methyl-4,5-dihydro-1H-benzoindole-3-carboxylic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N3-<2-(diethylamino)ethyl>-1-methyl-4,5-dihydro-1H-benzoindole-3-carboxamide
  参考文献：
  名称：

  Synthesis and D2-like binding affinity of 4,5-dihydro-1H-benzo[g]indole-3-carboxamide derivatives as conformationally restricted 5-phenyl-pyrrole-3-carboxamide analogs

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]-indole-3-carboxamide derivatives 2a-g were synthesized as conformationally restricted analogs of the dopamine D-2-like 5-phenylpyrrole-3-carboxamide ligands and evaluated for their affinity for the dopamine D-2-like receptors. In this series, N3-[(1-ethyltetrahydro-1H-2-pyrrolyl)methyl]-4,5-dihydro-1H-benzo[g]indole-3-carboxamide (2a) showed the highest affinity for D-2-like receptors (IC50 = 160 nM). Replacement of the N-(1-ethyl-2-pyrrolidinyl)methyl side chain with a 2-(N,N-diethylamino)ethyl or a 1-benzyl-4-piperidinyl group (2b, 2d) decreased affinity for the D-2-like receptor. The other compounds tested were found to be devoid of D-2-like binding affinity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00087-1
• 作为产物：
  描述：

  methyl 1-methyl-4,5-dihydro-1H-benzoindole-3-carboxylate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以84.2%的产率得到1-methyl-4,5-dihydro-1H-benzoindole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and D2-like binding affinity of 4,5-dihydro-1H-benzo[g]indole-3-carboxamide derivatives as conformationally restricted 5-phenyl-pyrrole-3-carboxamide analogs

  摘要：

  A series of 4,5-dihydro-1H-benzo[g]-indole-3-carboxamide derivatives 2a-g were synthesized as conformationally restricted analogs of the dopamine D-2-like 5-phenylpyrrole-3-carboxamide ligands and evaluated for their affinity for the dopamine D-2-like receptors. In this series, N3-[(1-ethyltetrahydro-1H-2-pyrrolyl)methyl]-4,5-dihydro-1H-benzo[g]indole-3-carboxamide (2a) showed the highest affinity for D-2-like receptors (IC50 = 160 nM). Replacement of the N-(1-ethyl-2-pyrrolidinyl)methyl side chain with a 2-(N,N-diethylamino)ethyl or a 1-benzyl-4-piperidinyl group (2b, 2d) decreased affinity for the D-2-like receptor. The other compounds tested were found to be devoid of D-2-like binding affinity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00087-1