(1S,3aR,6aS)-2-((S)-2-Isobutoxycarbonylamino-3,3-dimethyl-butyryl)-5,5-dimethyl-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid | 1026082-76-7

• 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: (1S,3aR,6aS)-2-((S)-2-Isobutoxycarbonylamino-3,3-dimethyl-butyryl)-5,5-dimethyl-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid
• 英文别名: (3S,3aS,6aR)-2-[(2S)-3,3-dimethyl-2-(2-methylpropoxycarbonylamino)butanoyl]-5,5-dimethyl-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-3-carboxylic acid
• CAS: 1026082-76-7
• 化学式: C₂₁H₃₆N₂O₅
• 分子量: 396.527
• InChiKey: ZIIOINWTOMEMJL-YHUYYLMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (1S,3aR,6aS)-2-((S)-2-Isobutoxycarbonylamino-3,3-dimethyl-butyryl)-5,5-dimethyl-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid 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 为溶剂， 生成 2-methylpropyl N-[(2S)-1-[(1S,3aR,6aS)-1-({1-[({[(S)-(dimethylcarbamoyl)(phenyl)methyl]carbamoyl}methyl)carbamoyl]-1-oxopentan-2-yl}carbamoyl)-5,5-dimethyl-octahydrocyclopenta[c]pyrrol-2-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Discovery of SCH446211 (SCH6):  A New Ketoamide Inhibitor of the HCV NS3 Serine Protease and HCV Subgenomic RNA Replication

  摘要：

  Introduction of various modified prolines at P-2 and optimization of the P-1 side chain led to the discovery of SCH6 (24, Table 2), a potent ketoamide inhibitor of the HCV NS3 serine protease. In addition to excellent enzyme potency (K-i* = 3.8 nM), 24 was also found to be a potent inhibitor of HCV subgenomic RNA replication with IC50 and IC90 of 40 and 100 nM, respectively. Recently, antiviral activity of 24 was demonstrated with inhibition of the full-length genotype 2a HCV genome. In addition, 24 was found to restore the responsiveness of the interferon regulatory factor 3 (IRF-3) in cells containing HCV RNA replicons.

  DOI：

  10.1021/jm060077j
• 作为产物：
  描述：

  N-isobutyloxycarbonyl(D/L)-tert-leucine 在 lithium hydroxide 、 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 、 二氯甲烷 为溶剂， 生成 (1S,3aR,6aS)-2-((S)-2-Isobutoxycarbonylamino-3,3-dimethyl-butyryl)-5,5-dimethyl-octahydro-cyclopenta[c]pyrrole-1-carboxylic acid
  参考文献：
  名称：

  Discovery of SCH446211 (SCH6):  A New Ketoamide Inhibitor of the HCV NS3 Serine Protease and HCV Subgenomic RNA Replication

  摘要：

  Introduction of various modified prolines at P-2 and optimization of the P-1 side chain led to the discovery of SCH6 (24, Table 2), a potent ketoamide inhibitor of the HCV NS3 serine protease. In addition to excellent enzyme potency (K-i* = 3.8 nM), 24 was also found to be a potent inhibitor of HCV subgenomic RNA replication with IC50 and IC90 of 40 and 100 nM, respectively. Recently, antiviral activity of 24 was demonstrated with inhibition of the full-length genotype 2a HCV genome. In addition, 24 was found to restore the responsiveness of the interferon regulatory factor 3 (IRF-3) in cells containing HCV RNA replicons.

  DOI：

  10.1021/jm060077j