ethyl N-(tert-butyloxycarbonyl)-N-(2-carbethoxyethyl)-3-amino-5-phenylvalerate | 134420-77-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl N-(tert-butyloxycarbonyl)-N-(2-carbethoxyethyl)-3-amino-5-phenylvalerate
• 英文别名: ethyl 3-[(3-ethoxy-3-oxopropyl)-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-phenylpentanoate
• CAS: 134420-77-2
• 化学式: C₂₃H₃₅NO₆
• 分子量: 421.534
• InChiKey: WVRBKEJCUVHKDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl N-(tert-butyloxycarbonyl)-N-(2-carbethoxyethyl)-3-amino-5-phenylvalerate 在 镍 氢气 、 sodium 作用下， 以 乙醇 、 苯 为溶剂， 25.0~80.0 ℃ 、6.08 MPa 条件下， 反应 24.0h， 生成 4-Hydroxy-6-phenethyl-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester
  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：

  丙烯酸乙酯 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.25h， 生成 ethyl N-(tert-butyloxycarbonyl)-N-(2-carbethoxyethyl)-3-amino-5-phenylvalerate
  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