2-Acetyl-4,6-diethylphloroglucin | 19687-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetyl-4,6-diethylphloroglucin
• 英文别名: 4.6-Diethyl-phloro-acetophenon；1-(3,5-Diethyl-2,4,6-trihydroxyphenyl)ethanone
• CAS: 19687-48-0
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: FIGMGYFUIQWTMH-UHFFFAOYSA-N

物化性质

• 熔点：
  106–109°C
• 沸点：
  420.6±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-Diethylphloroglucin 、 乙酰氯 在 三氯化铝 作用下， 生成 2-Acetyl-4,6-diethylphloroglucin
  参考文献：
  名称：

  Collins,E. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 96 - 101

  摘要：

  DOI：

文献信息

• Antitumor Agents 260. New Desmosdumotin B Analogues with Improved In Vitro Anticancer Activity
  作者：Kyoko Nakagawa-Goto、Kenneth F. Bastow、Tzu-Hsuan Chen、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/jm701208v

  日期：2008.6.1

  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.