{(S)-1-[((S)-cyclohexyl(methylcarbamoyl)methyl)methylcarbamoyl]-2,2-dimethylpropyl}carbamic acid tert-butyl ester | 925241-00-5

• 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: {(S)-1-[((S)-cyclohexyl(methylcarbamoyl)methyl)methylcarbamoyl]-2,2-dimethylpropyl}carbamic acid tert-butyl ester
• CAS: 925241-00-5
• 化学式: C₂₁H₃₉N₃O₄
• 分子量: 397.558
• InChiKey: IEFDTSIAVQLWOX-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  87.74
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[((S)-cyclohexyl(methylcarbamoyl)methyl)methylcarbamoyl]-2,2-dimethylpropyl}carbamic acid tert-butyl ester 、 三氟乙酸 在 三乙基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-N-((S)-(methylcarbamoyl)(cyclohexyl)methyl)-2-amino-N,3,3-trimethylbutyramide trifluoroacetic acid salt
  参考文献：
  名称：

  Synthesis of novel potent hepatitis C virus NS3 protease inhibitors: Discovery of 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a N-acyl-l-hydroxyproline bioisostere

  摘要：

  Potent tetrapeptidic inhibitors of the HCV NS3 protease have been developed incorporating 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a new N-acyl-L-hydroxyproline mimic. The hydroxycyclopentene template was synthesized in eight steps from commercially available, (syn)-tetrahydrophthalic anhydride. Three different amino acids were explored in the PI-position and in the P2-position the hydroxyl group of the cyclopentene template was substituted with 7-methoxy-2-phenyl-quinolin-4-ol. The P3/P4-positions were then optimized from a set of six amino acid derivatives. All inhibitors were evaluated in an in vitro assay using the full-length NS3 protease. Several potent inhibitors were identified, the most promising exhibiting a K-i value of 1.1 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.044
• 作为产物：
  描述：

  (S)-[cyclohexyl(methylcarbamoyl)methyl]methylcarbamic acid (9H-fluoren-9-yl)methyl ester 在 哌啶 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 {(S)-1-[((S)-cyclohexyl(methylcarbamoyl)methyl)methylcarbamoyl]-2,2-dimethylpropyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of novel potent hepatitis C virus NS3 protease inhibitors: Discovery of 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a N-acyl-l-hydroxyproline bioisostere

  摘要：

  Potent tetrapeptidic inhibitors of the HCV NS3 protease have been developed incorporating 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a new N-acyl-L-hydroxyproline mimic. The hydroxycyclopentene template was synthesized in eight steps from commercially available, (syn)-tetrahydrophthalic anhydride. Three different amino acids were explored in the PI-position and in the P2-position the hydroxyl group of the cyclopentene template was substituted with 7-methoxy-2-phenyl-quinolin-4-ol. The P3/P4-positions were then optimized from a set of six amino acid derivatives. All inhibitors were evaluated in an in vitro assay using the full-length NS3 protease. Several potent inhibitors were identified, the most promising exhibiting a K-i value of 1.1 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.044