(2S)-2-amino-N-[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-hydrazinyl-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pentanediamide

• 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)-2-amino-N-[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-hydrazinyl-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pentanediamide
• 化学式: C₃₈H₅₅N₉O₇S
• 分子量: 781.977
• InChiKey: HFKSUFPLWPBKTB-IFZIZQFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  55
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  286
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-N-[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-hydrazinyl-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pentanediamide 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 4.0h， 生成
  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：

  (2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid 在 三氟乙酸 作用下， 反应 0.5h， 生成 (2S)-2-amino-N-[(2S)-1-[[(2S)-1-[[(3R)-1-[(2S)-1-[[(2S)-1-hydrazinyl-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-2-oxopyrrolidin-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pentanediamide
  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

文献信息

• Cyclic peptides as selective tachykinin antagonists
  作者：Brian J. Williams、Neil R. Curtis、Alexander T. McKnight、Janet J. Maguire、Stephen C. Young、Daniel F. Veber、Raymond Baker

  DOI：10.1021/jm00053a001

  日期：1993.1

  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).