4-chloro-6-methyl-1,2,6,7-tetrahydro-benzo[2,3][1,4]diazepino[6,7,1-hi]indole | 71971-75-0

• 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: 4-chloro-6-methyl-1,2,6,7-tetrahydro-benzo[2,3][1,4]diazepino[6,7,1-hi]indole
• 英文别名: 4-chloro-6-methyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine；12-chloro-9-methyl-1,8-diazatetracyclo[8.6.1.02,7.014,17]heptadeca-2,4,6,10,12,14(17)-hexaene
• CAS: 71971-75-0
• 化学式: C₁₆H₁₅ClN₂
• 分子量: 270.762
• InChiKey: OJEBTGFBMOJAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-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 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(12-Chloro-9-methyl-1,8-diazatetracyclo[8.6.1.02,7.014,17]heptadeca-2,4,6,10,12,14(17)-hexaen-8-yl)-3-(methylamino)propan-1-one
  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
• 作为产物：
  描述：

  4-chloro-1,2-dihydro-6-methylindolo[1,7-ab][1,5]benzodiazepine hydrochloride 在 sodium borohydrid 作用下， 以 乙醇 、 水 为溶剂， 生成 4-chloro-6-methyl-1,2,6,7-tetrahydro-benzo[2,3][1,4]diazepino[6,7,1-hi]indole
  参考文献：
  名称：

  Indolo-,1,2-dihydroindolo-, and 1,2,6,7-tetrahydroindolo [1,7-ab][1,5]

  摘要：

  所披露的是##STR1##，其中X为氢、卤素或三氟甲基；Y为氢、卤素或三氟甲基；R为氢、较低烷基、环烷基、苯基、卤苯基、呋喃基、吡啶基、4-甲基哌嗪-1-乙基或苯基较低烷基；R.sup.1为氢；n和m独立地为0或1，但当m为1时，n不为0，并且当n和m为1时，环位置1和2之间的键和位置6和7之间的键分别饱和，当n和m为0时，键是不饱和的；其药学上可接受的酸盐；制备所述化合物的方法；包括所述化合物的药物组合物；使用这些化合物的治疗方法；以及其中间体。这些化合物可用作镇痛和抗炎药物，以及其他药用活性化合物的制备中间体。

  公开号：

  US04186199A1

文献信息

• GLAMKOWSKI E. J.; FORTUNATO J. M., J. HETEROCYCL. CHEM., 1979, 16, NO 5, 865-869
  作者：GLAMKOWSKI E. J.、 FORTUNATO J. M.

  DOI：——

  日期：——
• 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：——
• US4186199A
  申请人：——

  公开号：US4186199A

  公开（公告）日：1980-01-29
• Indolo-,1,2-dihydroindolo-, and 1,2,6,7-tetrahydroindolo [1,7-ab][1,5]
  申请人：American Hoechst Corporation

  公开号：US04186199A1

  公开（公告）日：1980-01-29

  What is disclosed are ##STR1## wherein X is hydrogen, halogen or trifluoromethyl; Y is hydrogen, halogen or trifluoromethyl; R is hydrogen, loweralkyl, cycloalkyl, phenyl, halophenyl, furyl, pyridinyl, 4-methylpiperazin-1-ylethyl or phenylloweralkyl; R.sup.1 is hydrogen; n and m are independently 0 or 1, but n is not 0 when m is 1, and the bonds between ring positions 1 and 2 and between positions 6 and 7 are respectively saturated when n and m are 1 and are unsaturated when n and m are 0; pharmaceutically acceptable acid addition salts thereof; methods of preparing said compounds; pharmaceutical compositions including said compounds; methods of treatment using the compounds; and intermediates therefor. These compounds are useful as analgesic and anti-inflammatory agents, as well as intermediates for the preparation of other pharmaceutically active compounds.

  所披露的是##STR1##，其中X为氢、卤素或三氟甲基；Y为氢、卤素或三氟甲基；R为氢、较低烷基、环烷基、苯基、卤苯基、呋喃基、吡啶基、4-甲基哌嗪-1-乙基或苯基较低烷基；R.sup.1为氢；n和m独立地为0或1，但当m为1时，n不为0，并且当n和m为1时，环位置1和2之间的键和位置6和7之间的键分别饱和，当n和m为0时，键是不饱和的；其药学上可接受的酸盐；制备所述化合物的方法；包括所述化合物的药物组合物；使用这些化合物的治疗方法；以及其中间体。这些化合物可用作镇痛和抗炎药物，以及其他药用活性化合物的制备中间体。
• 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.