N-nonanoyl-L-prolyl-L-tyrosine ethyl ester | 200954-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-nonanoyl-L-prolyl-L-tyrosine ethyl ester
• 英文别名: ethyl (2S)-3-(4-hydroxyphenyl)-2-[[(2S)-1-nonanoylpyrrolidine-2-carbonyl]amino]propanoate
• CAS: 200954-41-2
• 化学式: C₂₅H₃₈N₂O₅
• 分子量: 446.587
• InChiKey: VHLKEVPUORUXML-VXKWHMMOSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  661.7±55.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-nonanoyl-L-prolyl-L-tyrosine ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以62%的产率得到N-nonanoyl-L-prolyl-L-tyrosine amide
  参考文献：
  名称：

  Design of N-Acylprolyltyrosine “Tripeptoid” Analogues of Neurotensin as Potential Atypical Antipsychotic Agents

  摘要：

  A series of N-acylprolyltyrosine amides was designed as tripeptoid analogues of neurotensin. The substituted dipeptides were tested in vivo for antidopamine activity by their ability to inhibit the apomorphine-induced climbing in mice and the dopamine-induced extrapolatory behavior impairment in rats. The N-acylprolyltyrosine amides structure-activity relationships have indicated the size of the N-acyl group and the configuration of amino acids that are important for the activity. Pie found that the bioactivity has been increased dramatically when the n-hydrocarbon chain on the N-acyl group was increased from four to five carbon atoms, The activity seems to reside exclusively in the L-Tyr diastereomers. All of the compounds tested were inactive in the cataleptogenic action and did not exhibit the acute toxicity even at doses 500-1000 times higher than ED50 climbing test, On this basis, the N-acylprolyltyrosine amides could potentially be a novel class of atypical antipsychotic agents.

  DOI：

  10.1021/jm970217c
• 作为产物：
  描述：

  壬酰氯 在 N-乙基吗啉 、 氯甲酸异丁酯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 N-nonanoyl-L-prolyl-L-tyrosine ethyl ester
  参考文献：
  名称：

  Design of N-Acylprolyltyrosine “Tripeptoid” Analogues of Neurotensin as Potential Atypical Antipsychotic Agents

  摘要：

  A series of N-acylprolyltyrosine amides was designed as tripeptoid analogues of neurotensin. The substituted dipeptides were tested in vivo for antidopamine activity by their ability to inhibit the apomorphine-induced climbing in mice and the dopamine-induced extrapolatory behavior impairment in rats. The N-acylprolyltyrosine amides structure-activity relationships have indicated the size of the N-acyl group and the configuration of amino acids that are important for the activity. Pie found that the bioactivity has been increased dramatically when the n-hydrocarbon chain on the N-acyl group was increased from four to five carbon atoms, The activity seems to reside exclusively in the L-Tyr diastereomers. All of the compounds tested were inactive in the cataleptogenic action and did not exhibit the acute toxicity even at doses 500-1000 times higher than ED50 climbing test, On this basis, the N-acylprolyltyrosine amides could potentially be a novel class of atypical antipsychotic agents.

  DOI：

  10.1021/jm970217c

文献信息

• Design of <i>N</i>-Acylprolyltyrosine “Tripeptoid” Analogues of Neurotensin as Potential Atypical Antipsychotic Agents
  作者：Tatiana A. Gudasheva、Tatiana A. Voronina、Rita U. Ostrovskaya、Natalya I. Zaitseva、Nina A. Bondarenko、Vera K. Briling、Ludmila S. Asmakova、Grigory G. Rozantsev、Sergei B. Seredenin

  DOI：10.1021/jm970217c

  日期：1998.1.1

  A series of N-acylprolyltyrosine amides was designed as tripeptoid analogues of neurotensin. The substituted dipeptides were tested in vivo for antidopamine activity by their ability to inhibit the apomorphine-induced climbing in mice and the dopamine-induced extrapolatory behavior impairment in rats. The N-acylprolyltyrosine amides structure-activity relationships have indicated the size of the N-acyl group and the configuration of amino acids that are important for the activity. Pie found that the bioactivity has been increased dramatically when the n-hydrocarbon chain on the N-acyl group was increased from four to five carbon atoms, The activity seems to reside exclusively in the L-Tyr diastereomers. All of the compounds tested were inactive in the cataleptogenic action and did not exhibit the acute toxicity even at doses 500-1000 times higher than ED50 climbing test, On this basis, the N-acylprolyltyrosine amides could potentially be a novel class of atypical antipsychotic agents.