tert-butyl (2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indole-1-carboxylate | 945405-64-1

• 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 (2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indole-1-carboxylate
• CAS: 945405-64-1
• 化学式: C₃₀H₃₈N₄O₅
• 分子量: 534.656
• InChiKey: UAFZOAVSRVVOOO-SDHOMARFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  123.32
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indole-1-carboxylate 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 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 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,3aS,7aS)-N-(4-carbamimidoylbenzyl)-1-((2S,3R)-3-chloro-2-((R)-2-hydroxy-3-phenylpropanamido)-4-methylpentanoyl)octahydro-1H-indole-2-carboxamide
  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 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (2S,3aS,7aS)-2-((4-(N'-((benzyloxy)carbonyl)carbamimidoyl)benzyl)carbamoyl)octahydro-1H-indole-1-carboxylate
  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