2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside | 91288-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS: 91288-43-6
• 化学式: C₂₅H₂₉NO₈S
• 分子量: 503.573
• InChiKey: URMRMGXFRIAEQT-JYSSUKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以71%的产率得到2-naphthylmethyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  2-乙酰氨基-2-脱氧-D-葡萄糖的S-，N-和O-糖基衍生物，以及潜在的化疗药物和疏水性糖苷配基和N-乙酰基-β-D-氨基葡萄糖苷酶抑制剂。

  摘要：

  已经获得了2-乙酰氨基-2-脱氧-D-葡萄糖与疏水性糖苷配基的S-，N-和O-糖基衍生物作为潜在的血浆膜活性剂。将2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-β-D-吡喃葡萄糖（6）转化为苄基，二苯甲基，三苯甲基和其他硫代糖苷。酰化6得到金刚烷基和卤代乙酰基衍生物。从相应的6的NH2-1和OH-1类似物获得了一系列类似的N-和O-糖基衍生物，例如O-和N-二硝基苯基，O-和N-金刚烷基以及N-4-甲基亚苄基衍生物。发现几种N-和S-糖基衍生物可在体外抑制小鼠的乳腺腺癌（TA3）细胞以及牛肉肝中的N-乙酰基-β-D-氨基葡萄糖苷酶。

  DOI：

  10.1016/0008-6215(84)85124-1
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.17h， 生成 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Thioglycosides Are Efficient Metabolic Decoys of Glycosylation that Reduce Selectin Dependent Leukocyte Adhesion

  摘要：

  Metabolic decoys are synthetic analogs of naturally occurring biosynthetic acceptors. These compounds divert cellular biosynthetic pathways by acting as artificial substrates that usurp the activity of natural enzymes. While O-linked glycosides are common, they are only partially effective even at millimolar concentrations. In contrast, we report that N-acetylglucosamine (GlcNAc) incorporated into various thioglycosides robustly truncate cell surface N- and O-linked glycan biosynthesis at 10-100 mu M concentrations. The > 10-fold greater inhibition is in part due to the resistance of thioglycosides to hydrolysis by intracellular hexosaminidases. The thioglycosides reduce beta-galactose incorporation into lactosamine chains, cell surface sialyl Lewis-X expression, and leukocyte rolling on selectin substrates including inflamed endothelial cells under fluid shear. Treatment of granulocytes with thioglycosides prior to infusion into mouse inhibited neutrophil homing to sites of acute inflammation and bone marrow by similar to 80%-90%. Overall, thioglycosides represent an easy to synthesize class of efficient metabolic inhibitors or decoys. They reduce N-/O-linked glycan biosynthesis and inflammatory leukocyte accumulation.

  DOI：

  10.1016/j.chembiol.2018.09.012