4-Methyl-3,4,5,6-tetrahydro-1H-azepino[3,4,5-cd]indole | 123882-96-2

• 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: 4-Methyl-3,4,5,6-tetrahydro-1H-azepino[3,4,5-cd]indole
• 英文别名: 11-methyl-3,11-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene
• CAS: 123882-96-2
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: UNYZCCDZGZDKJH-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

• 作为反应物：
  描述：

  4-Methyl-3,4,5,6-tetrahydro-1H-azepino[3,4,5-cd]indole 在 硼烷四氢呋喃络合物 作用下， 以 三氟乙酸 为溶剂， 以84%的产率得到11-Methyl-3,11-diazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene
  参考文献：
  名称：

  对脑多巴胺和5-羟色胺受体具有高亲和力的叠氮吲哚衍生物。

  摘要：

  我们合成了20和21作为多巴胺受体拮抗剂SKF-83742的构象约束类似物，以及类似物6-9、16和18-22。尽管20和21处于非活性状态，但7、9和19显示出与D-1，D-2，S-2和α-1受体的强结合，以及体内的抗精神病活性。

  DOI：

  10.1016/s0960-894x(98)00138-3
• 作为产物：
  描述：

  N-[2-(1H-indol-4-yl)ethyl]formamide 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 40.0h， 生成 4-Methyl-3,4,5,6-tetrahydro-1H-azepino[3,4,5-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

• Azepinoindole derivatives with high affinity for brain dopamine and serotonin receptors
  作者：Bruce E Maryanoff、David F McComsey、Gregory E Martin、Richard P Shank

  DOI：10.1016/s0960-894x(98)00138-3

  日期：1998.4

  We synthesized 20 and 21 as conformationally constrained analogues of the dopamine receptor antagonist SKF-83742, as well as analogues 6-9, 16, and 18-22. Although 20 and 21 were inactive, 7, 9, and 19 showed strong binding to D-1, D-2, S-2, and alpha-1 receptors, as well as antipsychotic activity in vivo.

  我们合成了20和21作为多巴胺受体拮抗剂SKF-83742的构象约束类似物，以及类似物6-9、16和18-22。尽管20和21处于非活性状态，但7、9和19显示出与D-1，D-2，S-2和α-1受体的强结合，以及体内的抗精神病活性。
• 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.