(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(cyclohexylthio)-5-((E)-4-phenylbut-1-enylsulfonamido)-tetrahydro-2H-pyran-3,4-diyl diacetate | 1002105-79-4

• 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: (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(cyclohexylthio)-5-((E)-4-phenylbut-1-enylsulfonamido)-tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-cyclohexylsulfanyl-5-[[(E)-4-phenylbut-1-enyl]sulfonylamino]oxan-2-yl]methyl acetate
• CAS: 1002105-79-4
• 化学式: C₂₈H₃₉NO₉S₂
• 分子量: 597.751
• InChiKey: BAEIGWBZQPTLIN-ASAHFFSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(cyclohexylthio)-5-((E)-4-phenylbut-1-enylsulfonamido)-tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(E)-N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-4-phenylbut-1-ene-1-sulfonamide
  参考文献：
  名称：

  Synthesis of Natural Product-Inspired Inhibitors of Mycobacterium tuberculosis Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase

  摘要：

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.

  DOI：

  10.1021/jm070669h
• 作为产物：
  描述：

  4-phenyl-but-1E-ene-1-sulfonyl chloride 、 (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-amino-6-(cyclohexylthio)-tetrahydro-2H-pyran-3,4-diyl diacetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(cyclohexylthio)-5-((E)-4-phenylbut-1-enylsulfonamido)-tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis of Natural Product-Inspired Inhibitors of Mycobacterium tuberculosis Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase

  摘要：

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.

  DOI：

  10.1021/jm070669h