(S)-2-Amino-pentanedioic acid 5-amide 1-{[(S)-1-[(S)-1-({[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-amide} | 145484-73-7

• 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: (S)-2-Amino-pentanedioic acid 5-amide 1-{[(S)-1-[(S)-1-({[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-amide}
• CAS: 145484-73-7
• 化学式: C₃₈H₅₄N₁₀O₇S
• 分子量: 794.976
• InChiKey: SMVSRFJXDRIPQC-PZBSVLGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  56.0
• 可旋转键数：
  23.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  285.52
• 氢给体数：
  10.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-pentanedioic acid 5-amide 1-{[(S)-1-[(S)-1-({[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-amide} 在 盐酸 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-2-[(S)-2-(2-{(S)-2-[(S)-2-((S)-2-Amino-4-carbamoyl-butyrylamino)-3-(1H-indol-3-yl)-propionylamino]-3-phenyl-propionylamino}-acetylamino)-4-methyl-pentanoylamino]-4-methylsulfanyl-butyryl azide; hydrochloride
  参考文献：
  名称：

  Cyclic peptides as selective tachykinin antagonists

  摘要：

  Twenty homodetic cyclic peptides based on the C-terminal sequence of substance P were prepared (Table I) by a combination of solid-phase techniques and cyclizations using azide coupling Incorporation of dipeptide mimics based on substituted gamma-lactams were used in some cases to restrict their conformational mobility. Five of these cyclic peptides were shown to have high tachykinin antagonist activity (pA2 > 6) at NK-2 receptors (rat vas deferens). The two most potent of this series, XVII, cyclo(Gln-Trp-Phe-Gly-Leu-Met) (pA2 = 8.1), and I cyclo(Gln-Trp-Phe-(R)Gly[ANC-2]Leu-Met) (pA2 = 6.7), were selective for NK-2 receptors compared with the other tachykinin receptors (Table II).

  DOI：

  10.1021/jm00053a001
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 生成 (S)-2-Amino-pentanedioic acid 5-amide 1-{[(S)-1-[(S)-1-({[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-(1H-indol-3-yl)-ethyl]-amide}
  参考文献：
  名称：

  Cyclic peptides as selective tachykinin antagonists

  摘要：

  Twenty homodetic cyclic peptides based on the C-terminal sequence of substance P were prepared (Table I) by a combination of solid-phase techniques and cyclizations using azide coupling Incorporation of dipeptide mimics based on substituted gamma-lactams were used in some cases to restrict their conformational mobility. Five of these cyclic peptides were shown to have high tachykinin antagonist activity (pA2 > 6) at NK-2 receptors (rat vas deferens). The two most potent of this series, XVII, cyclo(Gln-Trp-Phe-Gly-Leu-Met) (pA2 = 8.1), and I cyclo(Gln-Trp-Phe-(R)Gly[ANC-2]Leu-Met) (pA2 = 6.7), were selective for NK-2 receptors compared with the other tachykinin receptors (Table II).

  DOI：

  10.1021/jm00053a001