10-[2-(2,4-dimethoxyphenyl)-2-oxoethylidene]-10H-anthracen-9-one | 1127184-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-[2-(2,4-dimethoxyphenyl)-2-oxoethylidene]-10H-anthracen-9-one
• 英文别名: 10-[2-(2,4-Dimethoxyphenyl)-2-oxoethylidene]anthracen-9-one
• CAS: 1127184-90-0
• 化学式: C₂₄H₁₈O₄
• 分子量: 370.405
• InChiKey: HKLFGRNGIGXVMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (10-oxo-10H-anthracen-9-ylidene)acetic acetyl chloride 、 间苯二甲醚 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以0.75 g的产率得到10-[2-(2,4-dimethoxyphenyl)-2-oxoethylidene]-10H-anthracen-9-one
  参考文献：
  名称：

  10-(2-oxo-2-Phenylethylidene)-10H-anthracen-9-ones as Highly Active Antimicrotubule Agents: Synthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization

  摘要：

  A series of 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones were synthesized and evaluated for interactions with tubulin and for antiproliferative activity against a panel of human and rodent tumor cell lines. The 4-methoxy analogue 17b was most potent, displaying IC50 values ranging from 40 to 80 nM, including multidrug resistant phenotypes, and had excellent activity as an inhibitor of tubulin polymerization (IC50 = 0.52 mu M). Concentration-dependent flow cytometric studies showed that KB/HeLa cells treated with 17b were arrested in the G2/M phases of the cell cycle (EC50 = 90 nM). In competition experiments, 17b strongly displaced [H-3]-colchicine from its binding site in the tubulin. The results obtained demonstrate that the anti proliferative activity is related to the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm801338r

文献信息

• 10-(2-<i>oxo</i>-2-Phenylethylidene)-10<i>H</i>-anthracen-9-ones as Highly Active Antimicrotubule Agents: Synthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization
  作者：Helge Prinz、Peter Schmidt、Konrad J. Böhm、Silke Baasner、Klaus Müller、Eberhard Unger、Matthias Gerlach、Eckhard G. Günther

  DOI：10.1021/jm801338r

  日期：2009.3.12

  A series of 10-(2-oxo-2-phenylethylidene)-10H-anthracen-9-ones were synthesized and evaluated for interactions with tubulin and for antiproliferative activity against a panel of human and rodent tumor cell lines. The 4-methoxy analogue 17b was most potent, displaying IC50 values ranging from 40 to 80 nM, including multidrug resistant phenotypes, and had excellent activity as an inhibitor of tubulin polymerization (IC50 = 0.52 mu M). Concentration-dependent flow cytometric studies showed that KB/HeLa cells treated with 17b were arrested in the G2/M phases of the cell cycle (EC50 = 90 nM). In competition experiments, 17b strongly displaced [H-3]-colchicine from its binding site in the tubulin. The results obtained demonstrate that the anti proliferative activity is related to the inhibition of tubulin polymerization.