cyclohexyl 2-acetamido-2-deoxy-1-thio-3,4,6-tri-O-acetyl-α-D-glucopyranoside | 479255-65-7

• 分子结构分类: 有机化合物
• 英文名称: cyclohexyl 2-acetamido-2-deoxy-1-thio-3,4,6-tri-O-acetyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-cyclohexylsulfanyloxan-2-yl]methyl acetate
• CAS: 479255-65-7
• 化学式: C₂₀H₃₁NO₈S
• 分子量: 445.534
• InChiKey: SAPZDNBXUFRHSK-LASHMREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  cyclohexyl 2-acetamido-2-deoxy-1-thio-3,4,6-tri-O-acetyl-α-D-glucopyranoside 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 cyclohexyl 2-deoxy-2-ethylamino-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  A Family of Mycothiol Analogues

  摘要：

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.

  DOI：

  10.1081/car-200059965
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 劳森试剂 、 偶氮二异丁腈 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 4.5h， 生成 cyclohexyl 2-acetamido-2-deoxy-1-thio-3,4,6-tri-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  巯基硫醇类似物的捷径。

  摘要：

  [结构：见正文]描述了一种简单的硫代巯基（1）硫糖苷类似物（2）的合成。评估2对结核分枝杆菌的Mycothiol S-共轭酰胺酶显示出良好的比活性（7500 nmol min（-）（1）mg-蛋白质（-）（1），而14200为1），表明2可以作为抗结核药物设计的起点。

  DOI：

  10.1021/ol0269796

文献信息

• Synthesis of Natural Product-Inspired Inhibitors of <i>Mycobacterium tuberculosis</i> Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase
  作者：Belhu B. Metaferia、Brandon J. Fetterolf、Syed Shazad-ul-Hussan、Matthew Moravec、Jeremy A. Smith、Satyajit Ray、Maria-Teresa Gutierrez-Lugo、Carole A. Bewley

  DOI：10.1021/jm070669h

  日期：2007.12.13

  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.