2-(3-(aminooxy)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(4-hydroxyphenyl)propanoic acid | 1573111-88-2

• 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: 2-(3-(aminooxy)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(4-hydroxyphenyl)propanoic acid
• 英文别名: Z-NCan-Tyr-OH
• CAS: 1573111-88-2
• 化学式: C₂₀H₂₃N₃O₇
• 分子量: 417.419
• InChiKey: LPJXPDLNMFSHGQ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  160.21
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  methyl 2-(3-(aminooxy)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(4-hydroxyphenyl)propanoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以72%的产率得到2-(3-(aminooxy)-2-(((benzyloxy)carbonyl)amino)propanamido)-3-(4-hydroxyphenyl)propanoic acid
  参考文献：
  名称：

  Kyotorphin analogues containing unnatural amino acids: synthesis, analgesic activity and computer modeling of their interactions with μ-receptor

  摘要：

  Kyotorphin (KTP; Tyr-Arg) an endogenous neuropeptide is potently analgesic when delivered directly to CNS. An effort to enhance the potency, enzymatic stability and improving bioavailability of KTP is the modification with unnatural amino acids. The aims of presented study were: (1) To synthesize new analogues of kyotorphin containing unnatural amino acids: norcanavaine (NCav) and norcanaline (NCan), structural analogues of arginine and ornithine, respectively; (2) To understand the influence of the arginine mimetics on the pharmacological properties of KTP analogues, through examination their effects on the paw pressure nociceptive threshold; (3) To find relationship between the structure and obtained biological effects of the all synthesized kyotorhin analogues, by molecular docking with mu-opioid receptor. As a result of our work four new kyotorphin analogues containing NCan and NCav were obtained. A correlation between the data from the in vivo test and docking results was found. This allows a better elucidation of the ligand-receptor interactions, the prediction of biological activity of the newly synthesized compounds, and to generate compounds with increased biological effects.

  DOI：

  10.1007/s00044-014-0953-9