(2R,3R,4R,5R)-2,5-bis(allylsulfanyl)-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxyindan-1-yl]hexanediamide

• 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)-2,5-bis(allylsulfanyl)-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxyindan-1-yl]hexanediamide
• 英文别名: (2R,3R,4R,5R)-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2,5-bis(prop-2-enylsulfanyl)hexanediamide
• 化学式: C₃₀H₃₆N₂O₆S₂
• 分子量: 584.758
• InChiKey: KCNUMUHYFUJGAS-YNMRTIPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S,3R,2'S,3'R)-3'-hydroxymethyl-([2,2]bioxiranyl-3-yl)methanol 在 ruthenium trichloride 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 高碘酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.09h， 生成 (2R,3R,4R,5R)-2,5-bis(allylsulfanyl)-3,4-dihydroxy-N,N'-bis[(1S,2R)-2-hydroxyindan-1-yl]hexanediamide
  参考文献：
  名称：

  Synthesis of Potent C₂-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents

  摘要：

  The synthesis of novel, potent diol-based HIV-1 protease inhibitors, having either -SAr, -SCH2-Ar, or -SCH2R groups as P1/P1' substituents is described. They can be prepared using a straightforward synthesis involving a thiol nucleophilic ring opening of a diepoxide. Inhibitor 13 was found to be a potent inhibitor of HIV-1 PR, showing good antiviral activity in a cell-based assay.

  DOI：

  10.1021/jm0011169

文献信息

• Synthesis of Potent <i>C</i>₂-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents
  作者：Anna Mühlman、Björn Classon、Anders Hallberg、Bertil Samuelsson

  DOI：10.1021/jm0011169

  日期：2001.10.1

  The synthesis of novel, potent diol-based HIV-1 protease inhibitors, having either -SAr, -SCH2-Ar, or -SCH2R groups as P1/P1' substituents is described. They can be prepared using a straightforward synthesis involving a thiol nucleophilic ring opening of a diepoxide. Inhibitor 13 was found to be a potent inhibitor of HIV-1 PR, showing good antiviral activity in a cell-based assay.