{(S)-1-[(S)-1-((S)-1-Benzyl-2-{(R)-2-[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester | 145554-98-9

• 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)-1-[(S)-1-((S)-1-Benzyl-2-{(R)-2-[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester
• 英文别名: Boc-Gln-Trp-Phe-D-Pro-Leu-Met-NHNH2；tert-butyl N-[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[(2R)-2-[[(2S)-1-[[(2S)-1-hydrazinyl-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]carbamate
• CAS: 145554-98-9
• 化学式: C₄₆H₆₆N₁₀O₉S
• 分子量: 935.158
• InChiKey: UQAKENGWAYMNMD-OZBJQVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  66
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  314
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(S)-1-((S)-1-Benzyl-2-{(R)-2-[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester 在 盐酸 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.05h， 生成 3-[(5S,8S,11S,14S,17S,19aR)-5-Benzyl-8-(1H-indol-3-ylmethyl)-17-isobutyl-14-(2-methylsulfanyl-ethyl)-4,7,10,13,16,19-hexaoxo-icosahydro-3a,6,9,12,15,18-hexaaza-cyclopentacyclooctadecen-11-yl]-propionamide
  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：

  (Fmoc-Phe-O)2O 、 (Fmoc-Leu)2O 、 [(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoyl] (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanylbutanoate 、 、 alkaline earth salt of/the/ methylsulfuric acid 生成 {(S)-1-[(S)-1-((S)-1-Benzyl-2-{(R)-2-[(S)-1-((S)-1-hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester
  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).