1,4-二氯-5-(苯基甲氧基)-9,10-蒽二酮 | 88303-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,4-二氯-5-(苯基甲氧基)-9,10-蒽二酮
• 英文名称: 1,4-dichloro-5-(phenylmethoxy)-9,10-anthracenedione
• 英文别名: 1,4-dichloro-5-(phenylmethoxy)-9,10-antracenedione；1,4-dichloro-5-phenylmethoxyanthracene-9,10-dione
• CAS: 88303-56-4
• 化学式: C₂₁H₁₂Cl₂O₃
• 分子量: 383.23
• InChiKey: QFQZEFKTFQCZOB-UHFFFAOYSA-N

物化性质

• 熔点：
  122-126 °C
• 沸点：
  572.3±50.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-二氯-5-(苯基甲氧基)-9,10-蒽二酮 在 palladium hydroxide - carbon 吡啶 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 21.0h， 生成 洛索蒽醌
  参考文献：
  名称：

  抗癌蒽吡唑类。改进了临床药物CI-937，CI-941和盐酸吡罗酮的合成

  摘要：

  据报道，用于合成大量蒽吡咯临床药物CI-937，CI-941和盐酸吡咯酮的改进方法。还报告了这些试剂和合成序列中间体的详细分析和光谱数据。

  DOI：

  10.1002/jhet.5570260117
• 作为产物：
  描述：

  1,4-二氯-5-羟基蒽-9,10-二酮 以93的产率得到1,4-二氯-5-(苯基甲氧基)-9,10-蒽二酮
  参考文献：
  名称：

  Substituted anthra(1,9-cd)pyrazol-6(2H)-ones

  摘要：

  公开号：

  EP0103381B1

文献信息

• Process for preparing substituted anthra[1,9-cd]pyrazol-6(2H)-ones
  申请人：Warner-Lambert Company

  公开号：US04672129A1

  公开（公告）日：1987-06-09

  An improved process for producing anthra[1,9-cd]-pyrazol-6(2H)-ones from 1,4-dichloro-5,8-disubstituted 9,10-anthracenediones. The process produces higher yields by using a new combination of protecting groups on the compounds which allows for easier and cleaner chromatographic resolution. The compounds produced have antibacterial, antifungal, antileukemic, and antitumor activity.

  一种从1,4-二氯-5,8-二取代9,10-蒽酮中生产蒽[1,9-cd]-吡唑-6(2H)-酮的改进工艺。该工艺通过在化合物上使用新的保护基组合，使色谱分离更加容易和清洁，从而产生更高的产量。所生产的化合物具有抗菌、抗真菌、抗白血病和抗肿瘤活性。
• Improved process for preparing substituted anthra[1,9-cd]-pyrazol-6(2H)-ones
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0244819A2

  公开（公告）日：1987-11-11

  An improved process for producing anthra[1,9-cd]­pyrazol-6(2H)-ones from 1,4-dichloro-5,8-disubstituted 9,10-anthracenediones. The process produces higher yields by using a new combination of protecting groups on the compounds which allows for easier and cleaner chromatographic resolution. The compounds produced have antibacterial, antifungal, antileukemic, and antitumor activity.

  一种从 1,4-二氯-5,8-二取代 9,10-蒽二酮生产蒽并[1,9-cd]吡唑-6(2H)-酮的改进工艺。该工艺在化合物上使用了新的保护基团组合，使色谱解析更简单、更干净，从而提高了产量。生产出的化合物具有抗菌、抗真菌、抗白血病和抗肿瘤活性。
• Effect of Modification of 6-[(Aminoalkyl)amino]-7H-benzo[e]-perimidin-7-ones on Their Cytotoxic Activity Toward Sensitive and Multidrug Resistant Tumor Cell Lines. Synthesis and Biological Evaluation
  作者：Maria Dzieduszycka、Sante Martelli、Małgorzata Arciemiuk、Maria M. Bontemps-Gracz、Agnieszka Kupiec、Edward Borowski

  DOI：10.1016/s0968-0896(01)00358-3

  日期：2002.4

  Benzoperimidines, a novel group of antitumor anthracenedione analogues, are of interest due to their ability to overcome multidrug resistance of tumor cells (Stefanska, B., Dzieduszycka, M., Bontemps-Gracz, M. M., Borowski, E., Martelli, S., Supino, R., Pratesi, G., De Cesare, MA., Zunino, F., Kusnierczyk, H., Radzikowski, Cz. J. Med. Chem. 1999, 42, 3494). Although the structural factor essential for exhibiting this desirable property is the presence in the molecule of a fused heterocyclic ring, the cytotoxicity against resistant cells is highly influenced by the nature and location of the substituents. A series of novel synthetic derivatives, comprising monohydroxylated benzoperimidines and 2-aminobenzoperimidines, allowed the establishment of an in vitro structure-activity relationship for a panel of leukemia sensitive, as well as P-gp dependent multidrug resistance (MDR) and multidrug resistance associated protein dependent resistance (MRP) resistant cell lines. The membrane affinity for the compounds has also been determined. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 5-[(Aminoalkyl)amino]-substituted anthra[1,9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation
  作者：H. D. Hollis Showalter、Judith L. Johnson、Leslie M. Werbel、Wilbur R. Leopold、Robert C. Jackson、Edward F. Elslager

  DOI：10.1021/jm00369a002

  日期：1984.3
• J. Med. Chem. 1984, 27, 253-255
  作者：

  DOI：——

  日期：——