2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dien-1-one | 69298-85-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: 2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dien-1-one
• 英文别名: 3-acetyl-5-methylfilicinic acid；2-Acetyl-4,4,6-trimethylcyclohexan-1,3,5-trion；Trimethyl-phloracetophenon
• CAS: 69298-85-7
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: AGZDIKCMKAWDMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dien-1-one 、 碘甲烷 生成 4-乙酰基-5-羟基-2,2,6,6-四甲基环己-4-烯-1,3-二酮
  参考文献：
  名称：

  Nowy,G. et al., Chemische Berichte, 1966, vol. 99, p. 2075 - 2082

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 、 碘甲烷 在 potassium methanolate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 2-acetyl-3,5-dihydroxy-4,6,6-trimethylcyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Nowy,G. et al., Chemische Berichte, 1966, vol. 99, p. 2075 - 2082

  摘要：

  DOI：

文献信息

• Synthesis of 3-(<i>p</i>-Hydroxycinnamoyl)-5-methylfilicinic Acid and Dehydro-3,3′-diacetyl-5,5′-methylenedifilicinic Acid
  作者：Heitaro Obara、Jun-ichi Onodera、Satoshi Abe、Takashi Saito

  DOI：10.1246/bcsj.53.289

  日期：1980.1

  In connection with studies on the structure of carthamin (1), two analogous compounds of 1, 3-(p-hydroxycinnamoyl)-5-methylfilicinic acid and dehydro3,3′-diacetyl-5,5′-methylenedifilicinic acid have been synthesized.

  结合对胭脂树橙（1）结构的研究，合成了两种类似的化合物：1,3-(对羟基肉桂酰基)-5-甲基菲林酸和脱氢3,3′-二乙酰基-5,5′-亚甲基二菲林酸。
• 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.