[(2R,3R,4aR,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate | 1350450-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4aR,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate
• CAS: 1350450-10-0
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: AFUYITFFCLEQCI-HWKXDMQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1S,2S,3S,4R)-2,3-[(2R,3R)-2,3-dimethoxybutan-2,3-dioxy]-5-hydroxymethyl-4,6-di-O-isopropylidene-5-cyclohexene-1,2,3,4-tetraol 在 咪唑 、 2,4,6-三甲基吡啶 、 重铬酸吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 71.0h， 生成 [(2R,3R,4aR,8S,8aS)-8-hydroxy-2,3-dimethoxy-2,3-dimethyl-5-oxo-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate
  参考文献：
  名称：

  Inhibition of Glutathione S-Transferase M1 by New Gabosine Analogues Is Essential for Overcoming Cisplatin Resistance in Lung Cancer Cells

  摘要：

  A new class of human GST inhibitors has been identified via rational design approach; we report their discovery, synthesis, inhibitory activity, and synergetic effect in combination with cisplatin against A549 lung cancer cell line. The results of this effort show that the lead 4-O-decyl-gabosine D (24) has optimum synergetic effect in A549 human lung adenocarcinoma epithelial cell and that this activity involves inhibition of glutathione S-transferase M1, apparently consistent with siRNA-mediated knockdown of GSTM1 gene.

  DOI：

  10.1021/jm201131n