5-methyl-3,4,5,6-tetrahydro-1H-azepino<5,4,3-cd>indole | 38073-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 5-methyl-3,4,5,6-tetrahydro-1H-azepino<5,4,3-cd>indole
• 英文别名: 5-Methyl-azepinoindol；5-methyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole；10-Methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene
• CAS: 38073-26-6
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: CLOHLCGYYLTLCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  methyl 3-(2-nitroethyl)-1H-indole-4-carboxylate 在 palladium on activated charcoal 氢气 作用下， 反应 16.0h， 生成 5-methyl-3,4,5,6-tetrahydro-1H-azepino<5,4,3-cd>indole
  参考文献：
  名称：

  1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor

  摘要：

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.

  DOI：

  10.1021/jm00164a026

文献信息

• The chemistry of indoles. XLIV. Synthetic study directed toward 3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indoles.
  作者：MASANORI SOMEI、MASAYUKI WAKIDA、TOSHIHARU OHTA

  DOI：10.1248/cpb.36.1162

  日期：——

  A simple synthetic metho which can provide 3, 4, 5, 6-tetrahydro-1H-azepinol[5, 4, 3-cd]indole derivatives having a carbon side chain at any desired position of the nucleus was developed. The method was applied to the preparation of 4- and 5-alkyl-3, 4, 5, 6-tetrahydro-1H-azepino[5, 4, 3-cd]indoles.

  开发了一种简单的合成方法，可以提供在核的任意所需位置具有碳侧链的3, 4, 5, 6-四氢-1H-氮杂二环[5, 4, 3-cd]吲哚衍生物。该方法被应用于制备4-和5-烷基-3, 4, 5, 6-四氢-1H-氮杂二环[5, 4, 3-cd]吲哚。
• SOMEI, MASANORI;WAKIDA, MASAYUKI;OHTA, TOSHIHARU, CHEM. AND PHARM. BULL., 36,(1988) N 3, 1162-1168
  作者：SOMEI, MASANORI、WAKIDA, MASAYUKI、OHTA, TOSHIHARU

  DOI：——

  日期：——
• 1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor
  作者：Robin D. Clark、Klaus K. Weinhardt、Jacob Berger、Lawrence E. Fisher、Christine M. Brown、Alison C. MacKinnon、Andrew T. Kilpatrick、Michael Spedding

  DOI：10.1021/jm00164a026

  日期：1990.2

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.