(2S,5S,9S,10R,14S)-14-N-allyloxycarbonylamino-9-N-carbobenzyloxyamino-5-((1S-1-carbamoyl-3-methylbutyl)aminocarbonyl)-10-methyl-2-(2-methylpropyl)-11-oxa-1,7-diazacyclopentadecan-3,8,12,15-tetraone | 628318-93-4

• 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,5S,9S,10R,14S)-14-N-allyloxycarbonylamino-9-N-carbobenzyloxyamino-5-((1S-1-carbamoyl-3-methylbutyl)aminocarbonyl)-10-methyl-2-(2-methylpropyl)-11-oxa-1,7-diazacyclopentadecan-3,8,12,15-tetraone
• 英文别名: prop-2-enyl N-[(2R,3S,7S,10S,13S)-7-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]carbamoyl]-2-methyl-10-(2-methylpropyl)-4,9,12,15-tetraoxo-3-(phenylmethoxycarbonylamino)-1-oxa-5,11-diazacyclopentadec-13-yl]carbamate
• CAS: 628318-93-4
• 化学式: C₃₆H₅₂N₆O₁₁
• 分子量: 744.842
• InChiKey: JWQJPYDDUJXSHL-CCSCBQILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  250
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,5S,9S,10R,14S)-14-N-allyloxycarbonylamino-9-N-carbobenzyloxyamino-5-((1S-1-carbamoyl-3-methylbutyl)aminocarbonyl)-10-methyl-2-(2-methylpropyl)-11-oxa-1,7-diazacyclopentadecan-3,8,12,15-tetraone 在 四(三苯基膦)钯 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 [(2R,3S,7S,10S,13S)-13-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-7-((S)-1-carbamoyl-3-methyl-butylcarbamoyl)-10-isobutyl-2-methyl-4,9,12,15-tetraoxo-1-oxa-5,11-diaza-cyclopentadec-3-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin

  摘要：

  Lactams 1 and 2 are readily formed from acyclic precursors in the presence of trypsin and chymotrypsin, respectively, identifying the macrocyclic ring system as a potential motif for constrained transition state analogue inhibitors of the serine peptidases. Ketone 3 was synthesized and shown to be a modest inhibitor of chymotrypsin (K-i = 220 muM), albeit 4-fold more potent than the acyclic hydroxy acid 25 (K-i = 1.5 mM as a mixture of epimers). A precursor (31) to the amino boronic acid 4 was also prepared; although this derivative was a potent inhibitor of chymotrypsin (K-i = 130 nM) by virtue of the boronic acid moiety, it showed no advantage over the des-amino analogue 32 (K-i = 120 nM), which is not capable of cyclizing.

  DOI：

  10.1021/jo034837z
• 作为产物：
  描述：

  Alloc-Asp-OtBu 在 盐酸 、 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (2S,5S,9S,10R,14S)-14-N-allyloxycarbonylamino-9-N-carbobenzyloxyamino-5-((1S-1-carbamoyl-3-methylbutyl)aminocarbonyl)-10-methyl-2-(2-methylpropyl)-11-oxa-1,7-diazacyclopentadecan-3,8,12,15-tetraone
  参考文献：
  名称：

  Synthesis and Evaluation of Macrocyclic Transition State Analogue Inhibitors for α-Chymotrypsin

  摘要：

  Lactams 1 and 2 are readily formed from acyclic precursors in the presence of trypsin and chymotrypsin, respectively, identifying the macrocyclic ring system as a potential motif for constrained transition state analogue inhibitors of the serine peptidases. Ketone 3 was synthesized and shown to be a modest inhibitor of chymotrypsin (K-i = 220 muM), albeit 4-fold more potent than the acyclic hydroxy acid 25 (K-i = 1.5 mM as a mixture of epimers). A precursor (31) to the amino boronic acid 4 was also prepared; although this derivative was a potent inhibitor of chymotrypsin (K-i = 130 nM) by virtue of the boronic acid moiety, it showed no advantage over the des-amino analogue 32 (K-i = 120 nM), which is not capable of cyclizing.

  DOI：

  10.1021/jo034837z