(2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid | 1048677-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid
• 英文别名: (2S)-Mdcp；(S)-3-(4-Carbamoyl-2,6-dimethyl-phenyl)-2-methyl-propionic acid；(2S)-3-(4-carbamoyl-2,6-dimethylphenyl)-2-methylpropanoic acid
• CAS: 1048677-16-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: QKKLPEJMOBSQDY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  H-c[D-Cys-Gly-Phe(p-NO2)-D-Cys]NH2*CF3CO2H 、 (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid 在 N-甲基吗啉 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2S)-Mdcp-c[D-Cys-Gly-Phe(pNO2)-D-Cys]NH2
  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
• 作为产物：
  描述：

  methyl (S)-3-(4-carbamoyl-2,6-dimethylphenyl)-2-methylpropanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以78%的产率得到(2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid
  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