(2S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH | 1048677-08-2

• 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: (2S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH
• 英文别名: (S)-2-{[(4R,7S,13S)-13-[(S)-3-(4-Carbamoyl-2,6-dimethyl-phenyl)-2-methyl-propionylamino]-7-(4-fluoro-benzyl)-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triaza-cyclotetradecane-4-carbonyl]-amino}-3-phenyl-propionic acid；(2S)-2-[[(4R,7S,13S)-13-[[(2S)-3-(4-carbamoyl-2,6-dimethylphenyl)-2-methylpropanoyl]amino]-7-[(4-fluorophenyl)methyl]-3,3,14,14-tetramethyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carbonyl]amino]-3-phenylpropanoic acid
• CAS: 1048677-08-2
• 化学式: C₄₃H₅₃FN₆O₈S₂
• 分子量: 865.06
• InChiKey: UWEUXBUDBJQKPS-LMSMQYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  60
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  277
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2S)-2-[[(2R)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-3-(4-carbamoyl-2,6-dimethylphenyl)-2-methylpropanoyl]amino]-3-methyl-3-sulfanylbutanoyl]amino]acetyl]amino]-3-(4-fluorophenyl)propanoyl]amino]-3-methyl-3-sulfanylbutanoyl]amino]-3-phenylpropanoic acid 在 potassium hexacyanochromate(III) 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 (2S)-Mdcp-c[D-Pen-Gly-Phe(pF)-Pen]-Phe-OH
  参考文献：
  名称：

  Novel Opioid Peptide Derived Antagonists Containing (2S)-2-Methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic Acid [(2S)-Mdcp]

  摘要：

  A synthesis of the novel tyrosine analogue (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp] (15) was developed. In (2S)-Mdcp, the amino and hydroxyl groups of 2',6'-dimethyltyrosine are replaced by a methyl and a carbamoyl group, respectively, and its substitution for Tyr(1) in opioid agonist peptides resulted in compounds showing antagonism at all three opioid receptors. The cyclic peptide (2S)Mdcp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys]NH2 (1) Was a potent and selective mu antagonist, whereas (2S)-Mdcp-C[D-Pen-GIy-Phe(pF)-Pen]-Phe-OH (3) showed subnanomolar delta antagonist activity and extraordinary delta selectivity.

  DOI：

  10.1021/jm8004702