N-(9,10-dioxo-4,5-dipropoxy-9,10-dihydroanthracen-2-yl)-2-iodoacetamide | 1537900-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9,10-dioxo-4,5-dipropoxy-9,10-dihydroanthracen-2-yl)-2-iodoacetamide
• 英文别名: BW-AQ-118；N-(9,10-dioxo-4,5-dipropoxyanthracen-2-yl)-2-iodoacetamide
• CAS: 1537900-22-3
• 化学式: C₂₂H₂₂INO₅
• 分子量: 507.325
• InChiKey: BEJHJNFDBJSEOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-chloro-N-(9,10-dioxo-4,5-dipropoxy-9,10-dihydroanthracen-2-yl)acetamide 在 sodium iodide 作用下， 以82%的产率得到N-(9,10-dioxo-4,5-dipropoxy-9,10-dihydroanthracen-2-yl)-2-iodoacetamide
  参考文献：
  名称：

  [EN] ANTHRAQUINONE ANALOGS AND METHODS OF MAKING AND USING THEREOF
  [FR] ANALOGUES D'ANTHRAQUINONE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  公开号：

  WO2014011753A3

文献信息

• Upregulation of p53 through induction of MDM2 degradation: Anthraquinone analogs
  作者：Alexander B. Draganov、Xiaoxiao Yang、Abiodun Anifowose、Ladie Kimberly C. De La Cruz、Chaofeng Dai、Nanting Ni、Weixuan Chen、Zeus De Los Santos、Lubing Gu、Muxiang Zhou、Binghe Wang

  DOI：10.1016/j.bmc.2019.07.019

  日期：2019.9

  study, a novel anthraquinone analog BW-AQ-101 was identified as a potent inducer of MDM2 degradation, leading to upregulation of p53 and apoptosis in cell culture studies. In animal models of acute lymphocytic leukemia, treatment with BW-AQ-101 led to complete disease remission. In this study, we systematically investigated the effect of substitution patterns of the core anthraquinone scaffold. Through

  在先前的研究中，新型蒽醌类似物BW-AQ-101被确定为MDM2降解的有效诱导剂，从而在细胞培养研究中导致p53上调和细胞凋亡。在急性淋巴细胞白血病的动物模型中，用BW-AQ-101治疗可完全缓解疾病。在这项研究中，我们系统地研究了核心蒽醌支架取代模式的影响。通过在两种白血病细胞系中的细胞毒性评估，已经检查了32种类似物的结构-活性关系。已经鉴定出几种具有与BW-AQ-101相当或更高的效力的类似物。Western印迹分析证实了有效化合物对MDM2-p53轴的作用。该研究还提出了进一步优化工作的新化学空间。
• 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：EP2872474B1

  公开（公告）日：2022-01-19