(R)-3-(4-(dimethylamino)cyclohex-1-enyl)-1H-indole-5-carbonitrile | 938050-01-2

• 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: (R)-3-(4-(dimethylamino)cyclohex-1-enyl)-1H-indole-5-carbonitrile
• 英文别名: 3-[(4R)-4-(dimethylamino)cyclohexen-1-yl]-1H-indole-5-carbonitrile
• CAS: 938050-01-2
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: RSNYUBDIPFPZKJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-(dimethylamino)cyclohex-1-enyl)-1H-indole-5-carbonitrile 、 对甲苯磺酰氯 在 sodium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors

  摘要：

  A series of indole tetrahydropyridine and indole cyclohexenylamines was prepared, and their binding affinities at the human serotonin transporter (SERT) were determined. In particular, a nitrile substituent at the C5 position of the indole ring gave potent SERT activity. The stereochemistry of the NN-dimethylamine substituent was determined for the most potent indole cyclohexenylamine, 6a. The enantiomers of 6a were energy minimized and compared to other conformationally restricted SSRIs. Compound 6a was found to give a dose-response similar to the SSRI fluoxetine in microdialysis studies in rats. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.040
• 作为产物：
  描述：

  4-二甲氨基环己酮 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (R)-3-(4-(dimethylamino)cyclohex-1-enyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors

  摘要：

  A series of indole tetrahydropyridine and indole cyclohexenylamines was prepared, and their binding affinities at the human serotonin transporter (SERT) were determined. In particular, a nitrile substituent at the C5 position of the indole ring gave potent SERT activity. The stereochemistry of the NN-dimethylamine substituent was determined for the most potent indole cyclohexenylamine, 6a. The enantiomers of 6a were energy minimized and compared to other conformationally restricted SSRIs. Compound 6a was found to give a dose-response similar to the SSRI fluoxetine in microdialysis studies in rats. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.040

文献信息

• Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors
  作者：Jeffrey A. Deskus、James R. Epperson、Charles P. Sloan、Joseph A. Cipollina、Pierre Dextraze、Jingfang Qian-Cutrone、Qi Gao、Baoqing Ma、Brett R. Beno、Gail K. Mattson、Thaddeus F. Molski、Rudolph G. Krause、Matthew T. Taber、Nicholas J. Lodge、Ronald J. Mattson

  DOI：10.1016/j.bmcl.2007.03.040

  日期：2007.6

  A series of indole tetrahydropyridine and indole cyclohexenylamines was prepared, and their binding affinities at the human serotonin transporter (SERT) were determined. In particular, a nitrile substituent at the C5 position of the indole ring gave potent SERT activity. The stereochemistry of the NN-dimethylamine substituent was determined for the most potent indole cyclohexenylamine, 6a. The enantiomers of 6a were energy minimized and compared to other conformationally restricted SSRIs. Compound 6a was found to give a dose-response similar to the SSRI fluoxetine in microdialysis studies in rats. (C) 2007 Elsevier Ltd. All rights reserved.