2-Cyclobutylmethyl-2-{(S)-1-[3,3-difluoro-1-(hydroxy-methoxycarbonyl-methyl)-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester | 820993-08-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 2-Cyclobutylmethyl-2-{(S)-1-[3,3-difluoro-1-(hydroxy-methoxycarbonyl-methyl)-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
• CAS: 820993-08-6
• 化学式: C₃₁H₄₅F₂N₃O₇
• 分子量: 609.711
• InChiKey: WZGZRXQDVNXHFP-CJFRUNADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  134.27
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-Cyclobutylmethyl-2-{(S)-1-[3,3-difluoro-1-(hydroxy-methoxycarbonyl-methyl)-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 叔丁醇 为溶剂， 反应 0.42h， 生成 (R)-2-Cyclobutylmethyl-2-[(S)-1-(3,3-difluoro-1-methoxyoxalyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  The Design and Enzyme-Bound Crystal Structure of Indoline Based Peptidomimetic Inhibitors of Hepatitis C Virus NS3 Protease

  摘要：

  The design of a series of peptidomimetic inhibitors of the hepatitis C virus NS3 protease is described. These inhibitors feature an indoline-2-carboxamide as a novel heterocyclic replacement for the P3 amino acid residue and N-terminal capping group of tripeptide based inhibitors. The crystal structure of the ternary NS3/NS4A/inhibitor complex for the most active molecule in this series highlights its suitability as an N-terminal capping group of a dipeptide inhibitor of the NS3 protease.

  DOI：

  10.1021/jm049435d
• 作为产物：
  描述：

  2-Cyclobutylmethyl-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 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 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 2-Cyclobutylmethyl-2-{(S)-1-[3,3-difluoro-1-(hydroxy-methoxycarbonyl-methyl)-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  The Design and Enzyme-Bound Crystal Structure of Indoline Based Peptidomimetic Inhibitors of Hepatitis C Virus NS3 Protease

  摘要：

  The design of a series of peptidomimetic inhibitors of the hepatitis C virus NS3 protease is described. These inhibitors feature an indoline-2-carboxamide as a novel heterocyclic replacement for the P3 amino acid residue and N-terminal capping group of tripeptide based inhibitors. The crystal structure of the ternary NS3/NS4A/inhibitor complex for the most active molecule in this series highlights its suitability as an N-terminal capping group of a dipeptide inhibitor of the NS3 protease.

  DOI：

  10.1021/jm049435d