tert-butyl ((2R,3R)-1-((2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indol-1-yl)-3-methyl-1-oxopentan-2-yl)carbamate | 945405-47-0

• 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: tert-butyl ((2R,3R)-1-((2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indol-1-yl)-3-methyl-1-oxopentan-2-yl)carbamate
• CAS: 945405-47-0
• 化学式: C₃₆H₄₉N₅O₆
• 分子量: 647.815
• InChiKey: ZVTWXSXWQSHMEB-FXLIOLNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  152.42
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2R,3R)-1-((2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indol-1-yl)-3-methyl-1-oxopentan-2-yl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以73%的产率得到tert-butyl ((2R,3R)-1-((2S,3aS,7aS)-2-((4-carbamimidoylbenzyl)carbamoyl)octahydro-1H-indol-1-yl)-3-methyl-1-oxopentan-2-yl)carbamate
  参考文献：
  名称：

  Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin

  摘要：

  Based on X-ray crystallographic data of complexes of chlorodysinosin A with the enzyme thrombin, a series of analogs were synthesized varying the nature of the P-1, P-2, and P-3 pharmacophoric sites and the central octahydroindole carboxyamide core. In general, introduction of a hydrophobic substituent on the D-leucine amide residue dramatically improved the inhibition of the enzyme. This is rationalized based on a better fit of the P-3 subunit in the hydrophobic S-3 enzyme site. Single digit nanomolar inhibition expressed as IC50 was observed for several analogs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.075
• 作为产物：
  描述：

  培哚普利杂质47 在 2,6-二甲基吡啶 、 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl ((2R,3R)-1-((2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indol-1-yl)-3-methyl-1-oxopentan-2-yl)carbamate
  参考文献：
  名称：

  Structure-based organic synthesis of unnatural aeruginosin hybrids as potent inhibitors of thrombin

  摘要：

  Based on X-ray crystallographic data of complexes of chlorodysinosin A with the enzyme thrombin, a series of analogs were synthesized varying the nature of the P-1, P-2, and P-3 pharmacophoric sites and the central octahydroindole carboxyamide core. In general, introduction of a hydrophobic substituent on the D-leucine amide residue dramatically improved the inhibition of the enzyme. This is rationalized based on a better fit of the P-3 subunit in the hydrophobic S-3 enzyme site. Single digit nanomolar inhibition expressed as IC50 was observed for several analogs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.075