| 1350449-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1350449-78-3
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: PBSHEJWHVWDFCM-VNAATALASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 pyridinium dichromate 作用下， 生成 [(2R,3R,4aR,8S,8aS)-2,3,8-trimethoxy-2,3-dimethyl-5-oxo-8,8a-dihydro-4aH-1,4-benzodioxin-6-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of chiral hydroxylated enones as potential anti-tumor agents

  摘要：

  A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.026
• 作为产物：
  描述：

  (6S,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 2,4,6-三甲基吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成
  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