tert-butyloxycarbonyl-L-prolyl-L-tyrosine amide | 200954-43-4

• 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: tert-butyloxycarbonyl-L-prolyl-L-tyrosine amide
• 英文别名: 1-(tert-Butoxycarbonyl)-L-prolyl-L-tyrosinamide；tert-butyl (2S)-2-[[(2S)-1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 200954-43-4
• 化学式: C₁₉H₂₇N₃O₅
• 分子量: 377.44
• InChiKey: AXMYGQXGTRHHES-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 tert-butyloxycarbonyl-L-prolyl-L-tyrosine amide 反应 0.25h， 以96%的产率得到L-prolyl-L-tyrosine amide trifluoroacetate
  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：

  L-酪氨酸甲酯盐酸盐 在 N-乙基吗啉 、 氨 、 氯甲酸异丁酯 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 tert-butyloxycarbonyl-L-prolyl-L-tyrosine amide
  参考文献：
  名称：

  Molecular design, synthesis and neuroleptic activity of dipeptide analogs of sulpride

  摘要：

  DOI：

  10.1007/bf02464272

文献信息

• ——
  作者：N. I. Zaitseva、V. P. Lezina、A. N. Ignashin、V. K. Briling、T. A. Gudasheva

  DOI：10.1023/a:1012707304680

  日期：——
• Molecular design, synthesis and neuroleptic activity of dipeptide analogs of sulpride
  作者：T. A. Gudasheva、N. I. Zaitseva、N. A. Bondarenko、I. É. Scherbakova、L. S. Asmakova、G. G. Rozantsev、R. U. Ostrovskaya、T. A. Voronina、S. B. Seredenin

  DOI：10.1007/bf02464272

  日期：1997.11
• 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.