2-propyl-5-carbethoxy-1,2,3,6-tetrahydropyridine hydrochloride | 134420-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-propyl-5-carbethoxy-1,2,3,6-tetrahydropyridine hydrochloride
• 英文别名: Ethyl 2-propyl-1,2,3,6-tetrahydropyridine-5-carboxylate;hydrochloride
• CAS: 134420-87-4
• 化学式: C₁₁H₁₉NO₂*ClH
• 分子量: 233.738
• InChiKey: MWRUMQWQVCVUSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-propyl-5-carbethoxy-1,2,3,6-tetrahydropyridine hydrochloride 在 盐酸 作用下， 反应 3.0h， 以50%的产率得到6-propylguvacine 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
• 作为产物：
  描述：

  3-(2-Ethoxycarbonyl-ethylamino)-hexanoic acid ethyl ester 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 32.25h， 生成 2-propyl-5-carbethoxy-1,2,3,6-tetrahydropyridine 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