(10-oxo-10H-anthracen-9-ylidene)acetic acetyl chloride | 1005791-15-0

• 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 acetyl chloride
• 英文别名: (10-oxo-10H-anthracen-9-ylidene)acetyl chloride；10-oxo-9(10H)-anthracenylideneacetyl chloride；10-oxo-9(10H)-anthracenylidene-acetyl chloride；2-(10-oxoanthracen-9-ylidene)acetyl chloride
• CAS: 1005791-15-0
• 化学式: C₁₆H₉ClO₂
• 分子量: 268.699
• InChiKey: RFZJLMRIKAGESC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (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， 反应 5.0h， 以43%的产率得到2,6-aceanthrylenedione
  参考文献：
  名称：

  蒽醌环状乙烯基2,6-乙酰蒽二酮的合成

  摘要：

  2,6- aceanthrylenedione（第一合成6），蒽醌的循环vinylog和用于与诸如1- phenylaceanthrylene -2,6-二酮的合成的有用的起始原料7，8，和9，进行说明。（10-Oxo-10 H-蒽-9-亚烷基）乙酰氯（5）在室温下在AlCl 3存在下分子内环化，得到6。我们发现6是一种抑制微管蛋白聚合的细胞毒性化合物。

  DOI：

  10.1021/jo1003983
• 作为产物：
  描述：

  蒽酮 在 哌啶 、 N,N-二甲基甲酰胺 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (10-oxo-10H-anthracen-9-ylidene)acetic acetyl chloride
  参考文献：
  名称：

  ANTHRACENE COMPOUNDS AND THEIR USE FOR TREATING BENIGN AND MALIGNANT TUMOR DISORDERS

  摘要：

  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。

  公开号：

  US20080051463A1

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.
• 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。
• Synthesis of 2,6-Aceanthrylenedione, a Cyclic Vinylog of Anthraquinone
  作者：Helge Prinz、Konrad J. Böhm、Klaus Müller

  DOI：10.1021/jo1003983

  日期：2010.6.4

  The first synthesis of 2,6-aceanthrylenedione (6), a cyclic vinylog of anthraquinone and a useful starting material for the synthesis of 1-phenylaceanthrylene-2,6-diones such as 7, 8, and 9, is described. (10-Oxo-10H-anthracen-9-ylidene) acetyl chloride (5) cyclizes intramolecularly at room temperature in the presence of AlCl3 to give 6. We found that 6 is a cytotoxic compound that inhibits tubulin

  2,6- aceanthrylenedione（第一合成6），蒽醌的循环vinylog和用于与诸如1- phenylaceanthrylene -2,6-二酮的合成的有用的起始原料7，8，和9，进行说明。（10-Oxo-10 H-蒽-9-亚烷基）乙酰氯（5）在室温下在AlCl 3存在下分子内环化，得到6。我们发现6是一种抑制微管蛋白聚合的细胞毒性化合物。