1-[(2R)-2-methyl-1,2,8,9,10,11-hexahydro[1,4]diazepino[6,7,1-jk]carbazol-3(4H)-yl]-1-ethanone | 422318-44-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[(2R)-2-methyl-1,2,8,9,10,11-hexahydro[1,4]diazepino[6,7,1-jk]carbazol-3(4H)-yl]-1-ethanone
• 英文别名: 1-[(8R)-8-methyl-7,10-diazatetracyclo[8.6.1.05,17.011,16]heptadeca-1,3,5(17),11(16)-tetraen-7-yl]ethanone
• CAS: 422318-44-3
• 化学式: C₁₈H₂₂N₂O
• 分子量: 282.385
• InChiKey: ATHUYGNRINERBP-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(2R)-2-methyl-1,2,8,9,10,11-hexahydro[1,4]diazepino[6,7,1-jk]carbazol-3(4H)-yl]-1-ethanone 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2R)-2-methyl-1,2,3,4,8,9,10,11-octahydro[1,4]diazepino[6,7,1-jk]carbazole
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100
• 作为产物：
  描述：

  (R)-2-(2-Amino-benzoylamino)-propionic acid ethyl ester 在 盐酸 、 lithium aluminium tetrahydride 、 TEA 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 73.5h， 生成 1-[(2R)-2-methyl-1,2,8,9,10,11-hexahydro[1,4]diazepino[6,7,1-jk]carbazol-3(4H)-yl]-1-ethanone
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100

文献信息

• [1,4]Diazepino [6,7,1-jk] carbazoles and derivatives
  申请人：American Home Products Corporation

  公开号：US20020086860A1

  公开（公告）日：2002-07-04

  This invention provides [1,4]diazepino[6,7,1-jk]carbazole compounds of the formula: 1 wherein: R 1 and R 2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, phenoyl or thiophenoyl; R 3 , R 4 , R 5 and R 6 are H, alkyl, cycloalkyl, alkoxy or cycloalkoxy; R 7 is H or alkyl; R 8 is H or alkyl; and the dashed line indicates an optional double bond; or a pharmaceutically acceptable salt thereof, as well as methods and pharmaceutical compositions utilizing them for the treatment or prevention of disorders such as obsessive-compulsive disorder, depression, anxiety, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  这项发明提供了一种公式为1的[1,4]二氮杂二环[6,7,1-jk]吲哚类化合物，其中：R1和R2为H、烷基、烷氧基、卤素、氟代烷基、—CN、—NH—SO2-烷基、—SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、苯甲酰基或硫代苯甲酰基；R3、R4、R5和R6为H、烷基、环烷基、烷氧基或环烷氧基；R7为H或烷基；R8为H或烷基；虚线表示可选的双键；或其药学上可接受的盐，以及利用它们用于治疗或预防强迫症、抑郁症、焦虑症、精神分裂症、偏头痛、睡眠障碍、饮食障碍、肥胖症、癫痫和脊髓损伤等疾病的方法和药物组合物。
• US6503900B2
  申请人：——

  公开号：US6503900B2

  公开（公告）日：2003-01-07
• Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor
  作者：Annmarie L. Sabb、Robert L. Vogel、Gregory S. Welmaker、Joan E. Sabalski、Joseph Coupet、John Dunlop、Sharon Rosenzweig-Lipson、Boyd Harrison

  DOI：10.1016/j.bmcl.2004.02.100

  日期：2004.5

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.