2'-methyl desmosdumotin B | 1032423-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2'-methyl desmosdumotin B
• 英文别名: 2-Methyl desmosdumotin B；5-hydroxy-6,8,8-trimethyl-2-(2-methylphenyl)chromene-4,7-dione
• CAS: 1032423-07-6
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: JXZAPJKDKZPIEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C₂₀H₂₂O₄ 在 硫酸 、 碘 、 二甲基亚砜 作用下， 反应 6.0h， 以48%的产率得到2'-methyl desmosdumotin B
  参考文献：
  名称：

  Antitumor Agents 260. New Desmosdumotin B Analogues with Improved In Vitro Anticancer Activity

  摘要：

  Sixteen analogues (3-16, 33, and 48) of the unique flavonoid desmosdumotin B (1) were prepared and evaluated as in vitro inhibitors of the human KB cancer cell line and its MDR subclone, KB-VIN. 6,8,8-Triethyl analogues 10-13 showed enhanced KB-VIN selectivity. In particular, 4'-alkyl derivatives 11 (4'-Me) and 12 (4'-Et) showed significant ED50 values of 0.03 and 0.025 mu g/mL, respectively, against KB-VIN with selectivities of > 460- and 320-fold compared with that of KB. This report is the first to describe compounds showing such high activity against MDR cells versus non-MDR cells. The unique activity of 1-analogues is likely MDR-mediated because cotreatment with verapamil, a P-gp inhibitor, partially reversed the selective toxicity of both 1 and 10. Interestingly, only 1-analogues with a naphthalene B-ring (8 and 14) showed significant cytotoxic activity against KB; and other cancer cell lines. Thus, 1-analogues might be a new class of potent drug candidates, especially as 11 and 12 express direct selective action against tumors expressing MDR.

  DOI：

  10.1021/jm701208v