1,8-dimethoxy-3-(4'-acetylphenyl)-anthraquinone | 1353384-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,8-dimethoxy-3-(4'-acetylphenyl)-anthraquinone
• 英文别名: 3-(4-Acetylphenyl)-1,8-dimethoxyanthracene-9,10-dione；3-(4-acetylphenyl)-1,8-dimethoxyanthracene-9,10-dione
• CAS: 1353384-31-2
• 化学式: C₂₄H₁₈O₅
• 分子量: 386.404
• InChiKey: APGBFJOHTFYIBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,8-dimethoxy-3-iodo-anthraquinone 、 4-乙酰基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到1,8-dimethoxy-3-(4'-acetylphenyl)-anthraquinone
  参考文献：
  名称：

  新型大黄酸类似物作为潜在的抗癌药

  摘要：

  合成了两个系列的大黄酸类似物，并在3位进行了修饰。使用MTT测定法评估它们的细胞毒性。在所有合成的化合物，一种化合物显示出最好的效力，与IC 50值的2.7μ中号对HeLa细胞系和0.6μ中号靠在MOLT4细胞系。

  DOI：

  10.1002/cmdc.201100384

文献信息

• Anthraquinone Analogs and Methods of Making and Using Thereof
  申请人：Georgia State University Research Foundation, Inc.

  公开号：US20150203442A1

  公开（公告）日：2015-07-23

  Rhein analogues that exhibit anti-proliferative activity, particular against cancer cells, are described herein. In some embodiments, the compounds contain a flat or planar ring system. Such rings system by facilitate non-covalent binding of the compounds to the DNA complex, such as by intercalation. In some embodiment, the compounds contain a flat or planar ring system as described above and one or more substituents which are alkylating moieties, electrophilic groups or Michael acceptors or groups which contain one or more alkylating moieties, electrophilic groups and/or Michael acceptors. The compounds described herein can also contain one more functional groups to improve the solubility of the compounds.

  本文描述了一些具有抗增殖活性的莱茵类似物，特别是对癌细胞。在某些实施例中，化合物含有一个平坦或平面环系统。这种环系统可以促进化合物与DNA复合物的非共价结合，例如通过插入作用。在某些实施例中，化合物包含如上所述的平坦或平面环系统和一个或多个取代基，这些取代基是烷基化合物、亲电性基团或迈克尔受体或含有一个或多个烷基化合物、亲电性基团和/或迈克尔受体的基团。本文所描述的化合物还可以含有一个或多个功能基团，以提高化合物的溶解度。
• Anthraquinone analogs and methods of making and using thereof
  申请人：Georgia State University Research Foundation, Inc.

  公开号：US10544090B2

  公开（公告）日：2020-01-28

  Rhein analogues that exhibit anti-proliferative activity, particular against cancer cells, are described herein. In some embodiments, the compounds contain a flat or planar ring system. Such rings system by facilitate non-covalent binding of the compounds to the DNA complex, such as by intercalation. In some embodiment, the compounds contain a flat or planar ring system as described above and one or more substituents which are alkylating moieties, electrophilic groups or Michael acceptors or groups which contain one or more alkylating moieties, electrophilic groups and/or Michael acceptors. The compounds described herein can also contain one more functional groups to improve the solubility of the compounds.

  本文介绍了具有抗增殖活性，尤其是抗癌细胞活性的大黄酸类似物。在某些实施方案中，化合物含有扁平或平面环系统。这种环系有助于化合物与 DNA 复合物的非共价结合，例如通过插层作用。在某些实施方案中，化合物含有上述平环或平面环系统以及一个或多个取代基，这些取代基为烷基化分子、亲电基团或迈克尔受体，或含有一个或多个烷基化分子、亲电基团和/或迈克尔受体的基团。本文所述的化合物还可以含有一个以上的官能团，以提高化合物的溶解度。
• ANTHRAQUINONE ANALOGS AND METHODS OF MAKING AND USING THEREOF
  申请人：Georgia State University Research Foundation, Inc.

  公开号：EP2872474A2

  公开（公告）日：2015-05-20
• [EN] ANTHRAQUINONE ANALOGS AND METHODS OF MAKING AND USING THEREOF<br/>[FR] ANALOGUES D'ANTHRAQUINONE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2014011753A2

  公开（公告）日：2014-01-16

  Rhein analogues that exhibit anti-proliferative activity, particular against cancer cells, are described herein. In some embodiments, the compounds contain a flat or planar ring system. Such rings system by facilitate non-covalent binding of the compounds to the DNA complex, such as by intercalation. In some embodiment, the compounds contain a flat or planar ring system as described above and one or more substituents which are alkylating moieties, electrophilic groups or Michael acceptors or groups which contain one or more alkylating moieties, electrophilic groups and/or Michael acceptors. The compounds described herein can also contain one more functional groups to improve the solubility of the compounds.
• Novel Rhein Analogues as Potential Anticancer Agents
  作者：Xiaochuan Yang、Guojing Sun、Chunhao Yang、Binghe Wang

  DOI：10.1002/cmdc.201100384

  日期：2011.12.9

  Two series of rhein analogues were synthesized with modification at the 3‐position. Their cytotoxicities were evaluated using an MTT assay. Among all the compounds synthesized, one compound showed the best potency, with an IC50 value of 2.7 μM against the HeLa cell line and 0.6 μM against the MOLT4 cell line.

  合成了两个系列的大黄酸类似物，并在3位进行了修饰。使用MTT测定法评估它们的细胞毒性。在所有合成的化合物，一种化合物显示出最好的效力，与IC 50值的2.7μ中号对HeLa细胞系和0.6μ中号靠在MOLT4细胞系。