H-Phe-Phg-NH2 | 1204418-06-3

• 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: H-Phe-Phg-NH2
• 英文别名: (2S)-2-amino-N-(2-amino-2-oxo-1-phenylethyl)-3-phenylpropanamide
• CAS: 1204418-06-3
• 化学式: C₁₇H₁₉N₃O₂
• 分子量: 297.357
• InChiKey: BSXGHLFMKBVNIF-MLCCFXAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 2-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)-2-phenylacetic acid 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以31%的产率得到H-Phe-Phg-NH2
  参考文献：
  名称：

  Discovery of Dipeptides with High Affinity to the Specific Binding Site for Substance P₁₋₇

  摘要：

  Substance P 1-7 (SP1-7, H-Arg-Pro-Lys-Pro-Gln-Gln-Phe-OH) is the major bioactive metabolite of substance P. The interest in this heptapeptide originates from the observation that it modulates, and in certain cases opposes the effects of the parent peptide. e.g., the nociceptive effect. The p-opioid receptor agonist endomorphin-2 (EM-2, H-Tyr-Pro-Phe-Phe-NH2) has been found to also interact with the specific binding site of SP1-7 with only a 10-fold lower affinity compared to the native peptide. Considering the smaller size of EM-2 compared to the target heptapeptide, it was selected as a lead compound in the development of low-molecular-weight ligands to the SP1-7 binding site. An alanine scan and truncation study led to the unexpected discovery of the dipeptide H-Phe-Phe-NH2 (K-i = 1.5 nM), having equal affinity as the endogenous heptapeptide SP1-7. Moreover, the studies show that the C-terminal phenylalanine amide is crucial for the affinity of the dipeptide.

  DOI：

  10.1021/jm901352b

文献信息

• [EN] THERAPEUTIC METHODS AND COMPOSITIONS EMPLOYING PEPTIDE COMPOUNDS<br/>[FR] PROCÉDÉS THÉRAPEUTIQUES ET COMPOSITIONS UTILISANT DES COMPOSÉS PEPTIDIQUES
  申请人：NYBERG FRED

  公开号：WO2010004535A2

  公开（公告）日：2010-01-14

  Methods for alleviating pain in a mammal, methods for alleviating a symptom associated with cessation or withdrawal from an addiction to a habit-forming drug in a mammal, methods for alleviating inflammation in a mammal, and methods for alleviating a symptom associated with a neuropsychiatric disorder, wherein the neuropsychiatric disorder is a cognitive deficiency or anxiety, in a mammal, comprise administering to the mammal a therapeutically effective amount of a peptide compound of Formula (I), Formula (II), or Formula (III), or a pharmaceutically acceptable salt thereof: Formula (I), Formula (II), Formula (III) as described herein. Pharmaceutical compositions which may be employed, inter alia, in such methods comprise a peptide compound of Formula (I), Formula (II), or Formula (III) and a pharmaceutically acceptable carrier.