1-hydroxy-2-(1-hydroxyethyl)-3,6,8-trimethoxyanthraquinone | 928818-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-2-(1-hydroxyethyl)-3,6,8-trimethoxyanthraquinone
• 英文别名: 1-Hydroxy-2-(1-hydroxyethyl)-3,6,8-trimethoxyanthracene-9,10-dione
• CAS: 928818-59-1
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: MJBSYKMZXOBEFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-hydroxy-2-(1-hydroxyethyl)-3,6,8-trimethoxyanthraquinone 在 pyridinium chlorochromate 吡啶 、 lithium hydride 、 高碘酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 33.0h， 生成 tri-O-methyltopopyrone C
  参考文献：
  名称：

  First total synthesis of topopyrone C

  摘要：

  The first synthesis of topopyrone C, a natural compound and inhibitor of Topoisomerase 1, has been carried out by Mars-chalk alkylation of 1-hydroxy-3,6,8-trimethoxyanthraquinone, followed by a Baker-Venkataraman chain elongation and an acidcatalyzed cyclization for the construction of the pyrone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.164
• 作为产物：
  描述：

  1-hydroxy-3,6,8-trimethoxy-9,10-dihydroanthraquinone 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 1-hydroxy-2-(1-hydroxyethyl)-3,6,8-trimethoxyanthraquinone
  参考文献：
  名称：

  First total synthesis of topopyrone C

  摘要：

  The first synthesis of topopyrone C, a natural compound and inhibitor of Topoisomerase 1, has been carried out by Mars-chalk alkylation of 1-hydroxy-3,6,8-trimethoxyanthraquinone, followed by a Baker-Venkataraman chain elongation and an acidcatalyzed cyclization for the construction of the pyrone ring. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.164

文献信息

• Synthesis and cytotoxic activity of a new series of topoisomerase I inhibitors
  作者：Sabrina Dallavalle、Sonia Gattinoni、Stefania Mazzini、Leonardo Scaglioni、Lucio Merlini、Stella Tinelli、Giovanni L. Beretta、Franco Zunino

  DOI：10.1016/j.bmcl.2007.12.055

  日期：2008.2

  A series of structurally simple analogues of natural topopyrone C were synthesized and tested for cytotoxic and topoisomerase I inhibitory activities. The removal of the hydroxyl groups at the 5 and 9 positions resulted in an increased cytotoxic potency and ability to stabilize topoisomerase-mediated cleavage. In addition, the results suggest that some structural features, such as the pyrone ring and

  合成了一系列天然拓朴酮C的结构简单的类似物，并测试了其对细胞毒性和拓扑异构酶I的抑制活性。在5和9位上羟基的去除导致增加的细胞毒性效力和稳定拓扑异构酶介导的裂解的能力。另外，结果表明某些结构特征，例如吡喃环和11位的极性基团是拓扑异构酶I抑制作用的基础。这些结构要求也与细胞毒性活性一致。
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.