(2S,3S)-3-Ethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester | 745015-58-1

• 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: (2S,3S)-3-Ethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• 英文别名: (2S,3S)-3-ethyl-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 745015-58-1
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: IUOXJABKAMHQNL-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Ethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (2S,3S)-3-Ethyl-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078
• 作为产物：
  描述：

  (2S,3R)-N-(叔-丁基氧羰基)-O-(叔-丁基)二甲基硅烷基-3,4-去氢-焦谷氨醇 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 jones reagent 、 copper(I) bromide dimethylsulfide complex 、 氢气 、 potassium carbonate 、 丙酮 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 乙酸乙酯 为溶剂， -78.0~-20.0 ℃ 、101.33 kPa 条件下， 生成 (2S,3S)-3-Ethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078

文献信息

• Pd-Catalyzed directed<i>CH</i>-(hetero)arylation of cyclic α-amino acids: effects of substituents and the ring size
  作者：Valeriia Hutskalova、Pavel K. Mykhailiuk

  DOI：10.1039/c9ob00393b

  日期：——

  A systematic study on the directed Pd-catalyzed (hetero)arylation of 26 substituted cyclic α-amino acids at the C(3)-atom was performed. For the first time, the 7- and 8-membered cyclic amino acids were introduced to C–H activation. 8-Aminoquinoline was used as a directing group. Effects of the ring size and the substituents on the reaction efficacy and stereoselectivity were studied.

  对C（3）原子上26个取代的环状α-氨基酸进行定向Pd催化（杂）芳基化的系统研究。首次将7元和8元环状氨基酸引入C–H激活。8-氨基喹啉用作指导基团。研究了环大小和取代基对反应效率和立体选择性的影响。
• Novel peptides as NS3-serine protease inhibitors of hepatitis C virus
  申请人：Saksena K. Anil

  公开号：US20070032433A1

  公开（公告）日：2007-02-08

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

  本发明揭示了具有HCV蛋白酶抑制活性的新化合物，以及制备这些化合物的方法。在另一种实施方式中，本发明揭示了包含这些化合物的药物组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。
• US7244721B2
  申请人：——

  公开号：US7244721B2

  公开（公告）日：2007-07-17