(6R,6aS,8R,9R,10aS,10bR)-6,8,9-trimethoxy-2,2,8,9-tetramethyl-6,6a,10a,10b-tetrahydro-4H-[1,4]dioxino[2,3-h][1,3]benzodioxine | 1350449-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,6aS,8R,9R,10aS,10bR)-6,8,9-trimethoxy-2,2,8,9-tetramethyl-6,6a,10a,10b-tetrahydro-4H-[1,4]dioxino[2,3-h][1,3]benzodioxine
• CAS: 1350449-66-9
• 化学式: C₁₇H₂₈O₇
• 分子量: 344.405
• InChiKey: OLZLKRXCBYUACB-DUUYBOGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R,6aS,8R,9R,10aS,10bR)-6,8,9-trimethoxy-2,2,8,9-tetramethyl-6,6a,10a,10b-tetrahydro-4H-[1,4]dioxino[2,3-h][1,3]benzodioxine 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以96%的产率得到
  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：

  5,5a-didehydro-2,3-O-[(2R,3R)-2,3-dimethoxybutane-2,3-diyl]-4,6-O-isopropylidene-5a-carba-β-D-xylohexopyranose 、 碘甲烷 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以94%的产率得到(6R,6aS,8R,9R,10aS,10bR)-6,8,9-trimethoxy-2,2,8,9-tetramethyl-6,6a,10a,10b-tetrahydro-4H-[1,4]dioxino[2,3-h][1,3]benzodioxine
  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

文献信息

• Inhibition of Glutathione <i>S</i>-Transferase M1 by New Gabosine Analogues Is Essential for Overcoming Cisplatin Resistance in Lung Cancer Cells
  作者：Chie-Hong Wang、Ho T. Wu、Hau M. Cheng、Tien-Jui Yen、I-Hsuan Lu、Hui Chuan Chang、Shu-Chuan Jao、Tony K. M. Shing、Wen-Shan Li

  DOI：10.1021/jm201131n

  日期：2011.12.22

  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.