1-oxo-2-methyl-5-methoxy-1,8,9,9a-tetrahydro-2H-indeno[1,7-cd]azepine | 123883-11-4

• 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: 1-oxo-2-methyl-5-methoxy-1,8,9,9a-tetrahydro-2H-indeno[1,7-cd]azepine
• 英文别名: 7-Methoxy-11-methyl-11-azatricyclo[6.4.1.04,13]trideca-4(13),5,7,9-tetraen-12-one
• CAS: 123883-11-4
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: OFLSRXNPJMUZCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxo-2-methyl-5-methoxy-1,8,9,9a-tetrahydro-2H-indeno[1,7-cd]azepine 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以96%的产率得到1-oxo-2-methyl-5-methoxy-1,3,4,8,9,9a-hexahydro-2H-indeno[1,7-cd]azepine
  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
• 作为产物：
  描述：

  6-甲氧基茚烷-1-羧酸 在 盐酸 、 草酰氯 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-oxo-2-methyl-5-methoxy-1,8,9,9a-tetrahydro-2H-indeno[1,7-cd]azepine
  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

• CLARK, ROBIN D.;BERGER, JACOB;WEINHARDT, KLAUS K.
  作者：CLARK, ROBIN D.、BERGER, JACOB、WEINHARDT, KLAUS K.

  DOI：——

  日期：——
• US4957914A
  申请人：——

  公开号：US4957914A

  公开（公告）日：1990-09-18
• 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.