N-(tert-butoxycarbonyl)-D-prolyl-L-tyrosine methyl ester | 200954-26-3

• 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-(tert-butoxycarbonyl)-D-prolyl-L-tyrosine methyl ester
• 英文别名: Boc-D-Pro-Tyr-OMe；tert-butyl (2R)-2-[[(2S)-3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 200954-26-3
• 化学式: C₂₀H₂₈N₂O₆
• 分子量: 392.452
• InChiKey: CYPHYULTVBDQML-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-D-prolyl-L-tyrosine methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以40%的产率得到N-(tert-butoxycarbonyl)-D-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：

  D-脯氨酸 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-(tert-butoxycarbonyl)-D-prolyl-L-tyrosine methyl 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

• 10.1007/s11426-024-2097-y
  作者：Wei, Wan-Jie、Wang, Xin-Yu、Tang, Hai-Tao、Cui, Fei-Hu、Wu, Yun-Qi、Pan, Ying-Ming

  DOI：10.1007/s11426-024-2097-y

  日期：——

  The synthesis and modification of peptides occupy a unique position in the field of drug development, and the functionalization of amino acids is a valuable strategy as an alternative to peptide modification. Currently, the development of tyrosine (Tyr) as a target amino acid is a major challenge in the field of chemistry. Herein, we report an electrochemical radical coupling reaction of labeling tyrosine-containing

  肽的合成和修饰在药物开发领域占据着独特的地位，而氨基酸的功能化是替代肽修饰的一种有价值的策略。目前，开发酪氨酸（Tyr）作为目标氨基酸是化学领域的重大挑战。在此，我们首次报道了用硫代氨基甲酸酯衍生物标记含酪氨酸活性药物和肽的电化学自由基偶联反应。这种三组分、一锅反应可以在简单、温和、清洁的电化学条件下顺利进行，适用于各种含Tyr的药物分子衍生物和肽的功能化。
• 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.