2-(3-cyano-1H-indol-5-yl)-cyclopent-1-enecarboxylic acid ethyl ester | 676273-50-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(3-cyano-1H-indol-5-yl)-cyclopent-1-enecarboxylic acid ethyl ester
• 英文别名: ethyl 2-(3-cyano-1H-indol-5-yl)cyclopentene-1-carboxylate
• CAS: 676273-50-0
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: FSZCXKTYCMAIDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  498.8±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-cyano-1H-indol-5-yl)-cyclopent-1-enecarboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 palladium on activated charcoal 、 水 、 氢气 、 三乙酰氧基硼氢化钠 、 1,2-二氯乙烷 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-[(1R,2R)-2-(methylaminomethyl)cyclopentyl]-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

  摘要：

  Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.045
• 作为产物：
  描述：

  5-溴-3-氰基吲哚 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 硼酸三丁酯 、 potassium hydride 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 2-(3-cyano-1H-indol-5-yl)-cyclopent-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

  摘要：

  Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.045

文献信息

• Compounds for the treatment of premature ejaculation
  申请人：——

  公开号：US20040063768A1

  公开（公告）日：2004-04-01

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salts or solvates thereof and pharmaceutically acceptable formulations comprising said compounds 1 useful for the treatment of premature ejaculation, depression, attention deficit hyperactivity disorder, obsessive-compulsive disorder, post-traumatic stress disorder and substance abuse disorders.

  本发明涉及式(I)化合物及其药用可接受的盐或溶剂化物，以及包含所述化合物的药用可接受配方，用于治疗早泄、抑郁症、注意力缺陷/多动症、强迫症、创伤后应激障碍和物质滥用障碍。
• US7105516B2
  申请人：——

  公开号：US7105516B2

  公开（公告）日：2006-09-12
• [EN] COMPOUNDS FOR THE TREATMENT OF PREMATURE EJACULATION<br/>[FR] COMPOSES PERMETTANT DE TRAITER L'EJACULATION PRECOCE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004026237A2

  公开（公告）日：2004-04-01

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable salts or solvates thereof and pharmaceutically acceptable formulations comprising said compounds [INSERT CHEMICAL STRUCTURE HERE] (I) useful for the treatment of premature ejaculation, depression, attention deficit hyperactivity disorder, obsessive-compulsive disorder, post-traumatic stress disorder and substance abuse disorders.
• Conformationally restricted homotryptamines. Part 6: Indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors
  作者：Jonathan L. Ditta、Derek J. Denhart、Jeffrey A. Deskus、James R. Epperson、Zhaoxing Meng、Qi Gao、Gail K. Mattson、Mellissa A. LaPaglia、Matthew T. Taber、Thaddeus F. Molski、Nicholas J. Lodge、Ronald J. Mattson、John E. Macor

  DOI：10.1016/j.bmcl.2013.03.045

  日期：2013.5

  Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds. (C) 2013 Elsevier Ltd. All rights reserved.