6-<3-(dimethylamino)propyl>-1,2,6,7-tetrahydroindolo<1,7-ab><1,5>benzodiazepine | 117513-50-5

• 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-<3-(dimethylamino)propyl>-1,2,6,7-tetrahydroindolo<1,7-ab><1,5>benzodiazepine
• 英文别名: N,N-dimethyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-propanamine；6-[3-(dimethylamino)propyl]-1,2,6,7-tetrahydroindolo(1,7-ab)[1,5]benzodiazepine；3-(1,8-diazatetracyclo[8.6.1.02,7.014,17]heptadeca-2,4,6,10,12,14(17)-hexaen-9-yl)-N,N-dimethylpropan-1-amine
• CAS: 117513-50-5
• 化学式: C₂₀H₂₅N₃
• 分子量: 307.439
• InChiKey: ZKAFIDWTTTUKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 6-<3-(dimethylamino)propyl>-1,2,6,7-tetrahydroindolo<1,7-ab><1,5>benzodiazepine 以 甲醇 、 乙醇 、 甲苯 为溶剂， 生成 N,N-Dimethyl-7-(phenylamino)carbonyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-propanamine hydrochloride
  参考文献：
  名称：

  Antiinflammatory and analgesic aminoalkyl tetracyclic benzodiazepines

  摘要：

  已公开的化合物的结构式为##STR1##其中X和Y分别是氢、较低的烷基、三氟甲基或卤素；Z是--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--或--CH.sub.2 CH.sub.2 CH.sub.2 --；n为1、2或3；R.sub.1是氢、较低的烷酰基、芳酰基、乙氧羰基、苯氧羰基、较低的烷基氨基羰基、芳基氨基羰基、较低的烷基或芳基甲基；R.sub.2是氢或较低的烷基；R.sub.3是氢、较低的烷基、乙氧羰基、较低的烷酰基或芳基较低的烷基，或R.sub.2和R.sub.3一起是异丙亚甲基；但当n为3时，X、Y和R.sub.1都是氢，Z是--CH.sub.2 CH.sub.2 --，R.sub.2和R.sub.3不能同时为甲基。这些化合物具有抗炎和镇痛活性。

  公开号：

  US04751223A1
• 作为产物：
  描述：

  magnesium,N,N-dimethylpropan-1-amine,chloride 、 1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine 以 四氢呋喃 为溶剂， 反应 0.5h， 以5.86 g的产率得到6-<3-(dimethylamino)propyl>-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

• Aminoalkyl tetracyclic benzodiazepines, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0268793A1

  公开（公告）日：1988-06-01

  There are disclosed compounds of the formula where X and Y are independently hydrogen, loweralkyl, trifluoromethyl or halogen; Z is -CH₂CH₂-, -CH=CH- or -CH₂CH₂CH₂-; n is 1, 2 or 3; R₁ is hydrogen, loweralkanoyl, aroyl, ethoxycarbonyl, phenoxycarbonyl, loweralkylaminocarbonyl, arylaminocarbonyl, loweralkyl or arylmethyl; R₂ is hydrogen or loweralkyl; R₃ is hydrogen, loweralkyl, ethoxycarbonyl, loweralkanoyl or arylloweralkyl, or R₂ and R₃ taken together is isopropylidene; with the proviso that when n is 3, X, Y and R₁ are all hydrogen and Z is -CH₂CH₂-, R₂ and R₃ can not both be methyl. These compounds display antiinflammatory and analgesic activities.

  公开了式中的化合物 其中 X 和 Y 独立地是氢、低级烷基、三氟甲基或卤素；Z 是 -CH₂CH₂-、-CH=CH- 或 -CH₂CH₂CH₂-；n 是 1、2 或 3；R₁ 是氢、低级烷酰基、芳基、乙氧基羰基、苯氧基羰基、低级烷基氨基羰基、芳基氨基羰基、低级烷基或芳基甲基；R₂ 是氢或低级烷基；R₃ 是氢、低级烷基、乙氧基羰基、低级烷酰基或芳基低级烷基，或 R₂ 和 R₃ 合在一起是亚异丙基；但当 n 为 3，X、Y 和 R₁ 均为氢且 Z 为 -CH₂CH₂- 时，R₂ 和 R₃ 不能均为甲基。这些化合物具有抗炎和镇痛活性。
• US4751223A
  申请人：——

  公开号：US4751223A

  公开（公告）日：1988-06-14
• Antiinflammatory and analgesic aminoalkyl tetracyclic benzodiazepines
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04751223A1

  公开（公告）日：1988-06-14

  There are disclosed compounds of the formula ##STR1## where X and Y are independently hydrogen, loweralkyl, trifluoromethyl or halogen; Z is --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 CH.sub.2 --; n is 1, 2 or 3; R.sub.1 is hydrogen, loweralkanoyl, aroyl, ethoxycarbonyl, phenoxycarbonyl, loweralkylaminocarbonyl, arylaminocarbonyl, loweralkyl or arylmethyl; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is hydrogen, loweralkyl, ethoxycarbonyl, loweralkanoyl or arylloweralkyl, or R.sub.2 and R.sub.3 taken together is isopropylidene; with the proviso that when n is 3, X, Y and R.sub.1 are all hydrogen and Z is --CH.sub.2 CH.sub.2 --, R.sub.2 and R.sub.3 can not both be methyl. These compounds display antiinflammatory and analgesic activities.

  已公开的化合物的结构式为##STR1##其中X和Y分别是氢、较低的烷基、三氟甲基或卤素；Z是--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--或--CH.sub.2 CH.sub.2 CH.sub.2 --；n为1、2或3；R.sub.1是氢、较低的烷酰基、芳酰基、乙氧羰基、苯氧羰基、较低的烷基氨基羰基、芳基氨基羰基、较低的烷基或芳基甲基；R.sub.2是氢或较低的烷基；R.sub.3是氢、较低的烷基、乙氧羰基、较低的烷酰基或芳基较低的烷基，或R.sub.2和R.sub.3一起是异丙亚甲基；但当n为3时，X、Y和R.sub.1都是氢，Z是--CH.sub.2 CH.sub.2 --，R.sub.2和R.sub.3不能同时为甲基。这些化合物具有抗炎和镇痛活性。
• 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.