Ethyl 5-phenyl-3-(phenylmethoxycarbonylamino)pentanoate | 543700-16-9

• 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: Ethyl 5-phenyl-3-(phenylmethoxycarbonylamino)pentanoate
• 英文别名: ethyl 5-phenyl-3-(phenylmethoxycarbonylamino)pentanoate
• CAS: 543700-16-9
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: RVVDGCHYAMOXFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 5-phenyl-3-(phenylmethoxycarbonylamino)pentanoate 在 盐酸 、 甲酸 作用下， 生成 3-amino-5-phenyl-valeric acid ; hydrochloride
  参考文献：
  名称：

  N-, α-, and β-Substituted 3-Aminopropionic acids: design, syntheses and antiseizure activities

  摘要：

  A treatment for epilepsy is proposed based on analogues of 3-aminopropionic acid (beta-alanine), a putative neurotransmitter in the central nervous system (CNS). A model three point pharmacophore was proposed based on modelling data obtained from the study of antagonists for both the glial gamma-aminobutyric acid (GABA)-uptake site and the glycine co-agonist site of N-methyl-D-aspartate (NMDA) receptor. Three series of 3-aminopropionic acids containing, N-, alpha-, and beta-substituents, were designed and synthesized to probe the position and the size of a lipophilic binding pocket within the proposed pharmacophore. These analogues were tested in vivo for both their antiseizure activities and their neurologic toxicities. Among the fourteen novel 3-aminopropionic acids synthesized, eight were found to have promising antiseizure activity. This study shows that substitution on the N-terminus confers the greatest antiseizure activity, particularly against pilocarpine-induced seizures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00330-9
• 作为产物：
  描述：

  氨基甲酸苄酯 在 三甲基氯硅烷 、 对甲苯磺酸 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 Ethyl 5-phenyl-3-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  N-, α-, and β-Substituted 3-Aminopropionic acids: design, syntheses and antiseizure activities

  摘要：

  A treatment for epilepsy is proposed based on analogues of 3-aminopropionic acid (beta-alanine), a putative neurotransmitter in the central nervous system (CNS). A model three point pharmacophore was proposed based on modelling data obtained from the study of antagonists for both the glial gamma-aminobutyric acid (GABA)-uptake site and the glycine co-agonist site of N-methyl-D-aspartate (NMDA) receptor. Three series of 3-aminopropionic acids containing, N-, alpha-, and beta-substituents, were designed and synthesized to probe the position and the size of a lipophilic binding pocket within the proposed pharmacophore. These analogues were tested in vivo for both their antiseizure activities and their neurologic toxicities. Among the fourteen novel 3-aminopropionic acids synthesized, eight were found to have promising antiseizure activity. This study shows that substitution on the N-terminus confers the greatest antiseizure activity, particularly against pilocarpine-induced seizures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00330-9

文献信息

• TiCl4-promoted addition of nucleophiles to open chain α-amidoalkylphenyl sulfones
  作者：Marino Petrini、Elisabetta Torregiani

  DOI：10.1016/j.tetlet.2005.07.031

  日期：2005.9

  Linear alpha-amidoalkylphenyl sulfones are converted into the corresponding N-acyliminium ions by treatment with TiCl4 at low temperature and then made to react with different nucleophiles such as allyltrimethylsilane, silyl ketene acetal, anisole and thiophene. (c) 2005 Elsevier Ltd. All rights reserved.
• N-, α-, and β-Substituted 3-Aminopropionic acids: design, syntheses and antiseizure activities
  作者：C.Y.K Tan、D Wainman、D.F Weaver

  DOI：10.1016/s0968-0896(02)00330-9

  日期：2003.1

  A treatment for epilepsy is proposed based on analogues of 3-aminopropionic acid (beta-alanine), a putative neurotransmitter in the central nervous system (CNS). A model three point pharmacophore was proposed based on modelling data obtained from the study of antagonists for both the glial gamma-aminobutyric acid (GABA)-uptake site and the glycine co-agonist site of N-methyl-D-aspartate (NMDA) receptor. Three series of 3-aminopropionic acids containing, N-, alpha-, and beta-substituents, were designed and synthesized to probe the position and the size of a lipophilic binding pocket within the proposed pharmacophore. These analogues were tested in vivo for both their antiseizure activities and their neurologic toxicities. Among the fourteen novel 3-aminopropionic acids synthesized, eight were found to have promising antiseizure activity. This study shows that substitution on the N-terminus confers the greatest antiseizure activity, particularly against pilocarpine-induced seizures. (C) 2002 Elsevier Science Ltd. All rights reserved.