6-methyl-7-[3-(4-phenylpiperazin-1-yl)propionyl]-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine | 74116-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 6-methyl-7-[3-(4-phenylpiperazin-1-yl)propionyl]-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine
• 英文别名: 1-(9-Methyl-1,8-diazatetracyclo[8.6.1.02,7.014,17]heptadeca-2,4,6,10,12,14(17)-hexaen-8-yl)-3-(4-phenylpiperazin-1-yl)propan-1-one
• CAS: 74116-92-0
• 化学式: C₂₉H₃₂N₄O
• 分子量: 452.599
• InChiKey: ALSUAKUAAVZZBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-methyl-1,2,6,7-tetrahydro-benzo[2,3][1,4]diazepino[6,7,1-hi]indole 在 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 6-methyl-7-[3-(4-phenylpiperazin-1-yl)propionyl]-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine
  参考文献：
  名称：

  7-(Aminoacyl) and 7-(aminoalkyl) derivatives of 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepines as potential antidepressant agents

  摘要：

  The synthesis of 7-(aminoacyl) and 7-(aminoalkyl) derivatives of 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepines is described. These compounds were evaluated for antidepressant activity by their ability to inhibit tetrabenazine-induced ptosis in mice. Many compounds were found to be active in this animal model, and structure-activity relationships are discussed. Two analogues in particular, one from the 7-(aminoacyl) series (13) and one from the 7-(aminoalkyl) series (26), were of comparable potency to the antidepressant drugs desipramine and amitriptyline.

  DOI：

  10.1021/jm00186a018

文献信息

• Substituted 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepines
  申请人：American Hoechst Corporation

  公开号：US04192874A1

  公开（公告）日：1980-03-11

  What is disclosed are 1,2,6,7-tetrahydroindolo[1,7-ab] [1,5]benzodiazepines of the formula ##STR1## wherein R is hydrogen, loweralkyl, or cycloalkyl; ##STR2## n is an integer from 1 to 3; R.sub.1 is hydrogen, loweralkyl, or phenylloweralkyl; R.sub.2 is hydrogen or loweralkyl; or R.sub.1 and R.sub.2 may be taken together with the nitrogen to which they are attached to form pyrrolidinyl, piperidino, morpholino, or phenylpiperazinyl; and R.sub.3 is loweralkyl; and the pharmaceutically acceptable acid addition salts thereof. These compounds are useful as antidepressants and as analgesic and anti-inflammatory agents.

  公开的是1,2,6,7-四氢吲唑并[1,7-ab][1,5]苯并二氮杂卓类化合物，其结构式如上，其中R为氢、低级烷基或环烷基；n为1至3的整数；R1为氢、低级烷基或苯基低级烷基；R2为氢或低级烷基；或者R1和R2可与其所连接的氮原子一起形成吡咯烷基、哌啶基、吗啉基或苯基哌嗪基；R3为低级烷基；以及其药学上可接受的酸加成盐。这些化合物可作为抗抑郁药以及镇痛和抗炎药物使用。
• GLAMKOWSKI E. J.; FORTUNATO J. M.; GEYER H. M., J. MED. CHEM., 1980, 23, NO 12, 1380-1386
  作者：GLAMKOWSKI E. J.、 FORTUNATO J. M.、 GEYER H. M.

  DOI：——

  日期：——
• US4192874A
  申请人：——

  公开号：US4192874A

  公开（公告）日：1980-03-11
• 7-(Aminoacyl) and 7-(aminoalkyl) derivatives of 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepines as potential antidepressant agents
  作者：Edward J. Glamkowski、James M. Fortunato、Harry M. Geyer

  DOI：10.1021/jm00186a018

  日期：1980.12

  The synthesis of 7-(aminoacyl) and 7-(aminoalkyl) derivatives of 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepines is described. These compounds were evaluated for antidepressant activity by their ability to inhibit tetrabenazine-induced ptosis in mice. Many compounds were found to be active in this animal model, and structure-activity relationships are discussed. Two analogues in particular, one from the 7-(aminoacyl) series (13) and one from the 7-(aminoalkyl) series (26), were of comparable potency to the antidepressant drugs desipramine and amitriptyline.