(1S,2R)-N-[2,3-dihydro-2-((2S,3S)-2-isobutyl-3-hydroxy-4-(N-Boc-(R)-pyrrolidin-2-yl)-1-oxobutoxy)inden-1-yl]-4-methylbenzene sulfonamide | 1228119-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-N-[2,3-dihydro-2-((2S,3S)-2-isobutyl-3-hydroxy-4-(N-Boc-(R)-pyrrolidin-2-yl)-1-oxobutoxy)inden-1-yl]-4-methylbenzene sulfonamide
• CAS: 1228119-08-1
• 化学式: C₃₃H₄₆N₂O₇S
• 分子量: 614.803
• InChiKey: GLFGMBNWDQUKJT-BANMPPSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  122.24
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-N-[2,3-dihydro-2-((2S,3S)-2-isobutyl-3-hydroxy-4-(N-Boc-(R)-pyrrolidin-2-yl)-1-oxobutoxy)inden-1-yl]-4-methylbenzene sulfonamide 在 lithium hydroxide monohydrate 、 水 、 双氧水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以95%的产率得到(2S,3S)-2-isobutyl-3-hydroxy-4-(N-Boc-(R)-pyrrolidin-2-yl)-butyric acid
  参考文献：
  名称：

  Evaluation of retro-inverso modifications of HTLV-1 protease inhibitors containing a hydroxyethylamine isoster

  摘要：

  Effects of retro-inverso (RI) modifications of HTLV-1 protease inhibitors containing a hydroxyethylamine isoster backbone were clarified. Construction of the isoster backbone was achieved by a stereoselective aldol reaction. Four diastereomers with different configurations at the isoster hydroxyl site and the scissile site substituent were synthesized. Inhibitory activities of the new inhibitors suggest that partially modified RI inhibitors would interact with HTLV-1 protease in the same manner as the parent hydroxyethylamine inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.019
• 作为产物：
  描述：

  tert-butyl (2R)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 、 (1S,2R)-cis-N-[2,3-dihydro-2-(4-methyl-1-oxopentyloxy)inden-1-yl]-4-methylbenzenesulfonamide 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以13%的产率得到(1S,2R)-N-[2,3-dihydro-2-((2S,3R)-2-isobutyl-3-hydroxy-4-(N-Boc-(R)-pyrrolidin-2-yl)-1-oxobutoxy)inden-1-yl]-4-methylbenzene sulfonamide
  参考文献：
  名称：

  Evaluation of retro-inverso modifications of HTLV-1 protease inhibitors containing a hydroxyethylamine isoster

  摘要：

  Effects of retro-inverso (RI) modifications of HTLV-1 protease inhibitors containing a hydroxyethylamine isoster backbone were clarified. Construction of the isoster backbone was achieved by a stereoselective aldol reaction. Four diastereomers with different configurations at the isoster hydroxyl site and the scissile site substituent were synthesized. Inhibitory activities of the new inhibitors suggest that partially modified RI inhibitors would interact with HTLV-1 protease in the same manner as the parent hydroxyethylamine inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.019