((2S,3S)-3-Ethyl-pyrrolidin-2-yl)-methanol | 696645-61-1

• 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: ((2S,3S)-3-Ethyl-pyrrolidin-2-yl)-methanol
• 英文别名: [(2S,3S)-3-ethylpyrrolidin-2-yl]methanol
• CAS: 696645-61-1
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: XKBPPBBBJDAAMJ-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-3-Ethyl-pyrrolidin-2-yl)-methanol 在 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 、 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 氢气 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-pyrrolidin-2-yl)-methanol
  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

• Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants
  作者：Robert B Perni、Luc J Farmer、Kevin M Cottrell、John J Court、Lawrence F Courtney、David D Deininger、Cynthia A Gates、Scott L Harbeson、Joseph L Kim、Chao Lin、Kai Lin、Yu-Ping Luong、John P Maxwell、Mark A Murcko、Janos Pitlik、B.Govinda Rao、Wayne C Schairer、Roger D Tung、John H Van Drie、Keith Wilson、John A Thomson

  DOI：10.1016/j.bmcl.2004.01.078

  日期：2004.4

  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.