(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-(2-trimethylsilanylethynyl-benzyloxy)-hexanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide] | 906071-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-(2-trimethylsilanylethynyl-benzyloxy)-hexanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide]
• CAS: 906071-60-1
• 化学式: C₄₈H₅₆N₂O₈Si₂
• 分子量: 845.152
• InChiKey: GOKRGJPVGNDFPW-OEWFRHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  60.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  157.58
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-(2-trimethylsilanylethynyl-benzyloxy)-hexanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide] 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以18.6 mg的产率得到
  参考文献：
  名称：

  A new structural theme in C2-symmetric HIV-1 protease inhibitors: ortho-Substituted P1/P1′ side chains

  摘要：

  In this report, the rapid syntheses of 24 novel C-2-symmetric HIV-1 protease inhibitors are described. Two ortho-iodobenzyloxy containing C-terminal duplicated inhibitors served as starting materials for microwave-enhanced palladium(0)-catalyzed carbon-carbon bond forming reactions (Suzuki, Sonogashira, Heck, and Negishi). Highly potent inhibitors equipped with ortho-functionalized P1/P1' side chains as the structural theme were identified. Computational efforts were applied to study the binding mode of this class of inhibitors and to establish structure-activity relationships. The overall orientation of the inhibitors in the active site was reproduced by docking which suggested three possible conformations of the P1/P1' groups of which two seem more plausible. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.045
• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 5.25h， 生成 (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-(2-trimethylsilanylethynyl-benzyloxy)-hexanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide]
  参考文献：
  名称：

  A new structural theme in C2-symmetric HIV-1 protease inhibitors: ortho-Substituted P1/P1′ side chains

  摘要：

  In this report, the rapid syntheses of 24 novel C-2-symmetric HIV-1 protease inhibitors are described. Two ortho-iodobenzyloxy containing C-terminal duplicated inhibitors served as starting materials for microwave-enhanced palladium(0)-catalyzed carbon-carbon bond forming reactions (Suzuki, Sonogashira, Heck, and Negishi). Highly potent inhibitors equipped with ortho-functionalized P1/P1' side chains as the structural theme were identified. Computational efforts were applied to study the binding mode of this class of inhibitors and to establish structure-activity relationships. The overall orientation of the inhibitors in the active site was reproduced by docking which suggested three possible conformations of the P1/P1' groups of which two seem more plausible. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.045