6-phenethylguvacine hydrochloride | 134420-90-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 6-phenethylguvacine hydrochloride
• 英文别名: 2-(2-Phenylethyl)-1,2,3,6-tetrahydropyridine-5-carboxylic acid;hydrochloride
• CAS: 134420-90-9
• 化学式: C₁₄H₁₇NO₂*ClH
• 分子量: 267.755
• InChiKey: YZUXYPVSPOBFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 3-amino-5-phenylvalerate 在 镍 盐酸 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 氢气 、 sodium 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 苯 为溶剂， 80.0 ℃ 、6.08 MPa 条件下， 反应 33.25h， 生成 6-phenethylguvacine hydrochloride
  参考文献：
  名称：

  GABA-uptake inhibitors: construction of a general pharmacophore model and successful prediction of a new representative

  摘要：

  A model for the pharmacophore of GABA-uptake inhibitors was established using published structure-activity data and molecular modeling. The model accounted for the activities of different classes of GABA-uptake inhibitors. Analogues of guvacine substituted at position 6 were synthesized in order to confirm the model. 6-(3,3-Diphenylpropyl)guvacine (30f), which fit well with the pharmacophore, had an in vitro IC50 of 0.1-mu-M. This value is as good as those of the best GABA-uptake inhibitors known today.

  DOI：

  10.1021/jm00112a032

文献信息

• GABA-uptake inhibitors: construction of a general pharmacophore model and successful prediction of a new representative
  作者：Victor N'Goka、Gilbert Schlewer、Jean Michel Linget、Jean Pierre Chambon、Camille Georges Wermuth

  DOI：10.1021/jm00112a032

  日期：1991.8

  A model for the pharmacophore of GABA-uptake inhibitors was established using published structure-activity data and molecular modeling. The model accounted for the activities of different classes of GABA-uptake inhibitors. Analogues of guvacine substituted at position 6 were synthesized in order to confirm the model. 6-(3,3-Diphenylpropyl)guvacine (30f), which fit well with the pharmacophore, had an in vitro IC50 of 0.1-mu-M. This value is as good as those of the best GABA-uptake inhibitors known today.