(4S,5S)-4-ethyl-5-(hydroxymethyl)pyrrolidin-2-one | 745014-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5S)-4-ethyl-5-(hydroxymethyl)pyrrolidin-2-one
• CAS: 745014-11-3
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: PMSMYMWVYTVOTC-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-ethyl-5-(hydroxymethyl)pyrrolidin-2-one 在 lithium aluminium tetrahydride 、 jones reagent 、 硫酸 、 potassium carbonate 、 丙酮 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S)-3-Ethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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 、 copper(I) bromide dimethylsulfide complex 、 氢气 作用下， 以 乙醚 、 乙醇 、 乙酸乙酯 为溶剂， -78.0~-20.0 ℃ 、101.33 kPa 条件下， 生成 (4S,5S)-4-ethyl-5-(hydroxymethyl)pyrrolidin-2-one
  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

• Bicyclic-Fused Heteroaryl or Aryl Compounds
  申请人：Pfizer Inc.

  公开号：US20150284405A1

  公开（公告）日：2015-10-08

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物的异构体和药学上可接受的盐已被披露，其中所述化合物具有如规范中定义的Ia式结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。
• [EN] BICYCLIC-FUSED HETEROARYL OR ARYL COMPOUNDS AND THEIR USE AS IRAK4 INHIBITORS<br/>[FR] COMPOSÉS À BASE D'HÉTÉROARYLE OU D'ARYLE FUSIONNÉ-BICYCLIQUE ET LEUR UTILISATION COMME COMPOSÉS INHIBITEURS DE L'IRAK 4
  申请人：PFIZER

  公开号：WO2015150995A1

  公开（公告）日：2015-10-08

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  该专利披露了具有Ia式结构的化合物、互变异构体和药学上可接受的盐，其定义在说明书中。还披露了相应的制药组合物、治疗方法、合成方法和中间体。
• Bicyclic-fused heteroaryl or aryl compounds
  申请人：Pfizer Inc.

  公开号：US10329302B2

  公开（公告）日：2019-06-25

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本发明公开了化合物、化合物的同系物和药学上可接受的盐，其中化合物具有说明书中定义的式 Ia 结构。 还公开了相应的药物组合物、治疗方法、合成方法和中间体。
• BICYCLIC-FUSED HETEROARYL OR ARYL COMPOUNDS AND THEIR USE AS IRAK4 INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP3126330A1

  公开（公告）日：2017-02-08
• US9458168B2
  申请人：——

  公开号：US9458168B2

  公开（公告）日：2016-10-04