(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-6-(cyclohexylthio)-tetrahydro-2H-pyran-3,4-diyl diacetate | 1002105-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-6-(cyclohexylthio)-tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-cyclohexylsulfanyl-5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoyl]amino]oxan-2-yl]methyl acetate
• CAS: 1002105-54-5
• 化学式: C₃₃H₄₈N₂O₁₀S
• 分子量: 664.818
• InChiKey: XCAUDKSUAJNGCS-ILRBKQRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-6-(cyclohexylthio)-tetrahydro-2H-pyran-3,4-diyl diacetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-amino-6-(cyclohexylthio)-tetrahydro-2H-pyran-3,4-diyl diacetate 、 Boc-L-高苯丙氨酸 在 N,N-二异丙基乙胺 、 焦碳酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)-6-(cyclohexylthio)-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