[(2R,3R,4aR,8S,8aS)-2,3-dimethoxy-2,3-dimethyl-5-oxo-8-phenylmethoxy-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate | 1350449-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,4aR,8S,8aS)-2,3-dimethoxy-2,3-dimethyl-5-oxo-8-phenylmethoxy-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate
• CAS: 1350449-84-1
• 化学式: C₂₂H₂₈O₈
• 分子量: 420.46
• InChiKey: LBRRFEIRONDERY-GLOJMNGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4aR,8S,8aS)-2,3-dimethoxy-2,3-dimethyl-5-oxo-8-phenylmethoxy-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以76%的产率得到[(3S,4R,5R)-4,5-dihydroxy-6-oxo-3-phenylmethoxycyclohexen-1-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
• 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 2,4,6-三甲基吡啶 、 重铬酸吡啶 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 40.0h， 生成 [(2R,3R,4aR,8S,8aS)-2,3-dimethoxy-2,3-dimethyl-5-oxo-8-phenylmethoxy-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