2-(2-tert-Butoxycarbonyl-thiophen-3-ylmethyl)-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester | 252357-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-tert-Butoxycarbonyl-thiophen-3-ylmethyl)-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester
• 英文别名: 1-[(2-methylpropan-2-yl)oxycarbonyl]-2-[[2-[(2-methylpropan-2-yl)oxycarbonyl]thiophen-3-yl]methyl]-3H-indole-2-carboxylic acid
• CAS: 252357-57-6
• 化学式: C₂₄H₂₉NO₆S
• 分子量: 459.563
• InChiKey: FMOORNQQYZOQQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-tert-Butoxycarbonyl-thiophen-3-ylmethyl)-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 在 戴斯-马丁氧化剂 、 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 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 39.0h， 生成 3-({N-[(2-{[2-(tertbutoxycarbonyl)thien-3-yl]methyl}-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：

  2,3-Dihydro-indole-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 在 palladium on activated charcoal 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 18.5h， 生成 2-(2-tert-Butoxycarbonyl-thiophen-3-ylmethyl)-2,3-dihydro-indole-1,2-dicarboxylic acid 1-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.