[(10-oxo-(10H)-anthracen-9-ylidene)]-acetic acid 2,6-dimethoxy-phenyl ester | 1127185-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [(10-oxo-(10H)-anthracen-9-ylidene)]-acetic acid 2,6-dimethoxy-phenyl ester
• 英文别名: (2,6-Dimethoxyphenyl) 2-(10-oxoanthracen-9-ylidene)acetate
• CAS: 1127185-00-5
• 化学式: C₂₄H₁₈O₅
• 分子量: 386.404
• InChiKey: SYMYXAGCXXSLBP-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  591.6±50.0 °C(predicted)
• 密度：
  1.317±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二甲氧基苯酚 、 (10-oxo-10H-anthracen-9-ylidene)acetic acetyl chloride 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以1.02 g的产率得到[(10-oxo-(10H)-anthracen-9-ylidene)]-acetic acid 2,6-dimethoxy-phenyl ester
  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

• ANTHRACENE COMPOUNDS AND THEIR USE FOR TREATING BENIGN AND MALIGNANT TUMOR DISORDERS
  申请人：Gerlach Matthias

  公开号：US20080051463A1

  公开（公告）日：2008-02-28

  The present invention provides novel anthracene compounds according to the formulae (I) and (II) and also selected anthracene compound compounds. The present invention furthermore provides a process for preparing such anthracene compounds. Also provided are pharmaceutical formulations comprising these anthracene compounds. The anthracene compounds provided are particularly suitable for the treatment and/or prophylaxis of physiological and/or pathophysiological conditions which can be treated by inhibiting tubulin polymerization and/or by inhibiting microtubuli-based motor proteins, in particular various tumor disorders.

  本发明提供了根据式(I)和(II)的新型蒽醌化合物，还提供了选定的蒽醌化合物。本发明还提供了制备这些蒽醌化合物的方法。还提供了包含这些蒽醌化合物的药物配方。提供的蒽醌化合物特别适用于治疗和/或预防可以通过抑制微管聚合和/或抑制微管基础马达蛋白来治疗的生理和/或病理生理状况，特别是各种肿瘤疾病。
• 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.