1-(4,4-Diphenylbut-3-enyl)-3-fluoropiperidine-3-carboxylic acid | 1265901-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4,4-Diphenylbut-3-enyl)-3-fluoropiperidine-3-carboxylic acid
• CAS: 1265901-12-9
• 化学式: C₂₂H₂₄FNO₂
• 分子量: 353.436
• InChiKey: KYVIFZVYZUQCME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4-溴-1-苯基丁-1-烯基)苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N-二异丙基乙胺 、 sodium hydroxide 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 乙醇 、 乙醚 为溶剂， 生成 1-(4,4-Diphenylbut-3-enyl)-3-fluoropiperidine-3-carboxylic acid
  参考文献：
  名称：

  Stereospecific synthesis and structure–activity relationships of unsymmetrical 4,4-diphenylbut-3-enyl derivatives of nipecotic acid as GAT-1 inhibitors

  摘要：

  Two complementary stereospecific synthetic approaches for the preparation of unsymmetrical ortho-substituted N-(4,4-diphenylbut-3-enyl) derivatives of nipecotic acid are described. Determination of the activity of the prepared compounds at the GAT-1 transporter highlighted differing SAR requirements of the E- and Z-phenyl rings, and led to the discovery of a compound with comparable potency to tiagabine. Some attempts to replace nipecotic acid with alternative novel amino acids are also described. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.09.025

文献信息

• Stereospecific synthesis and structure–activity relationships of unsymmetrical 4,4-diphenylbut-3-enyl derivatives of nipecotic acid as GAT-1 inhibitors
  作者：Domenica A. Pizzi、Colin P. Leslie、Romano Di Fabio、Catia Seri、Giovanni Bernasconi、Michela Squaglia、Gennaro Carnevale、Alessandro Falchi、Elisabetta Greco、Laura Mangiarini、Michele Negri

  DOI：10.1016/j.bmcl.2010.09.025

  日期：2011.1

  Two complementary stereospecific synthetic approaches for the preparation of unsymmetrical ortho-substituted N-(4,4-diphenylbut-3-enyl) derivatives of nipecotic acid are described. Determination of the activity of the prepared compounds at the GAT-1 transporter highlighted differing SAR requirements of the E- and Z-phenyl rings, and led to the discovery of a compound with comparable potency to tiagabine. Some attempts to replace nipecotic acid with alternative novel amino acids are also described. (C) 2010 Published by Elsevier Ltd.