oleyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 1332704-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: oleyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(Z)-octadec-9-enoxy]oxan-2-yl]methyl acetate
• CAS: 1332704-67-2
• 化学式: C₃₂H₅₅NO₉
• 分子量: 597.79
• InChiKey: XAPAACBRZHLSBH-HOOONLDESA-N

物化性质

• 沸点：
  682.8±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  42
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  oleyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到oleyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity

  摘要：

  The synthesis and biological activity of oleylN-acetyl-alpha- and beta-n-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the a-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

  DOI：

  10.1021/jm200961q
• 作为产物：
  描述：

  油醇 、 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 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 25.17h， 以48%的产率得到oleyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Antimitotic Thioglycosides: In Vitro and in Vivo Evaluation of Their Anticancer Activity

  摘要：

  The synthesis and biological activity of oleylN-acetyl-alpha- and beta-n-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the a-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

  DOI：

  10.1021/jm200961q