2-benzyl-1-tert-butyl-2-{[2-(tert-butoxycarbonyl)thien-3-yl]methyl}indoline-1,2-dicarboxylate | 252357-60-1

• 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: 2-benzyl-1-tert-butyl-2-{[2-(tert-butoxycarbonyl)thien-3-yl]methyl}indoline-1,2-dicarboxylate
• 英文别名: 2-O-benzyl 1-O-tert-butyl 2-[[2-[(2-methylpropan-2-yl)oxycarbonyl]thiophen-3-yl]methyl]-3H-indole-1,2-dicarboxylate
• CAS: 252357-60-1
• 化学式: C₃₁H₃₅NO₆S
• 分子量: 549.688
• InChiKey: DKYICWWXACCDEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-tert-butyl-2-{[2-(tert-butoxycarbonyl)thien-3-yl]methyl}indoline-1,2-dicarboxylate 在 palladium on activated charcoal 氢气 、 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 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 57.0h， 生成 3-(2-{(S)-1-[1-(Carboxy-dihydroxy-methyl)-3,3-difluoro-propylcarbamoyl]-3-methyl-butylcarbamoyl}-2,3-dihydro-1H-indol-2-ylmethyl)-thiophene-2-carboxylic acid
  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：

  tert-butyl 3-bromomethylthiophene-2-carboxylate 、 2,3-Dihydro-indole-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以85%的产率得到2-benzyl-1-tert-butyl-2-{[2-(tert-butoxycarbonyl)thien-3-yl]methyl}indoline-1,2-dicarboxylate
  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.