2-((S)-1-Carboxy-3-methyl-butylcarbamoyl)-2-cyclobutylmethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester | 1028286-55-6

• 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: 2-((S)-1-Carboxy-3-methyl-butylcarbamoyl)-2-cyclobutylmethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester
• 英文别名: (2S)-2-[[2-(cyclobutylmethyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]-3H-indole-2-carbonyl]amino]-4-methylpentanoic acid
• CAS: 1028286-55-6
• 化学式: C₂₅H₃₆N₂O₅
• 分子量: 444.571
• InChiKey: LSYUTGPHUOLSOI-UBDBMELISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((S)-1-Carboxy-3-methyl-butylcarbamoyl)-2-cyclobutylmethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 17.42h， 生成 3-({N-[(2-(cyclobutylmethyl)-2,3-dihydro-1H-indol-2-yl)carbonyl]-L-leucyl}amino)-5,5-difluoro-2-oxopentanoic acid trifluoroacetate
  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-甲基-1,2-吲哚啉羧酸-1-叔丁酯 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 双(三甲基硅烷基)氨基钾 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 34.5h， 生成 2-((S)-1-Carboxy-3-methyl-butylcarbamoyl)-2-cyclobutylmethyl-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

文献信息

• The Design and Enzyme-Bound Crystal Structure of Indoline Based Peptidomimetic Inhibitors of Hepatitis C Virus NS3 Protease
  作者：Jesus M. Ontoria、Stefania Di Marco、Immacolata Conte、M. Emilia Di Francesco、Cristina Gardelli、Uwe Koch、Victor G. Matassa、Marco Poma、Christian Steinkühler、Cinzia Volpari、Steven Harper

  DOI：10.1021/jm049435d

  日期：2004.12.1

  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.