(2S,2'S,3S,3'S)-[2,2']bioxiranyl-3,3'-dicarboxylic acid bis-[(1S)-2-methyl-1-(methylcarbamoyl)propylamide] | 372969-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,2'S,3S,3'S)-[2,2']bioxiranyl-3,3'-dicarboxylic acid bis-[(1S)-2-methyl-1-(methylcarbamoyl)propylamide]
• 英文别名: (2S,3R)-N-[(2S)-3-methyl-1-(methylamino)-1-oxobutan-2-yl]-3-[(2R,3S)-3-[[(2S)-3-methyl-1-(methylamino)-1-oxobutan-2-yl]carbamoyl]oxiran-2-yl]oxirane-2-carboxamide
• CAS: 372969-63-6
• 化学式: C₁₈H₃₀N₄O₆
• 分子量: 398.459
• InChiKey: IJVZCBMLNQWTPD-GHEKHTLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氟苯硫酚 、 (2S,2'S,3S,3'S)-[2,2']bioxiranyl-3,3'-dicarboxylic acid bis-[(1S)-2-methyl-1-(methylcarbamoyl)propylamide] 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76%的产率得到(2R,3R,4R,5R)-2,5-bis[(2-fluorophenyl)sulfanyl]-3,4-dihydroxy-N,N'-bis[(1S)-2-methyl-1-(methylcarbamoyl)propyl]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
• 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 、 高碘酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.67h， 生成 (2S,2'S,3S,3'S)-[2,2']bioxiranyl-3,3'-dicarboxylic acid bis-[(1S)-2-methyl-1-(methylcarbamoyl)propylamide]
  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.