1-羟基-2-(羟甲基)-6,8-二甲氧基-3-甲基蒽-9,10-二酮 | 851056-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-羟基-2-(羟甲基)-6,8-二甲氧基-3-甲基蒽-9,10-二酮
• 英文名称: 1-hydroxy-2-(hydroxymethyl)-6,8-dimethoxy-3-methylanthracene-9,10-dione
• 英文别名: 6,8-dimethoxy-1-hydroxy-2-hydroxymethyl-3-methyl-9,10-anthraquinone
• CAS: 851056-53-6
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: KJDPBNIAANPRQV-UHFFFAOYSA-N

物化性质

• 沸点：
  597.3±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-羟基-2-(羟甲基)-6,8-二甲氧基-3-甲基蒽-9,10-二酮 在 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 22.5h， 生成 (E)-3-(but-2-enyl)-5-fluoro-1-((1,6,8-trimethoxy-3-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and antitumor activity of conjugates of 5-Fluorouracil and emodin

  摘要：

  A series of conjugates of 5-Fluorouracil (5-FU) and emodin were synthesized by coupling trimethyl emodin with N-1, N-3 dialkylated 5-FU. The 5-FU moiety contained various substituents at the N-3-position were linked to the 2-position of trimethyl emodin via a methylene linkage. Their cytotoxicity against three cancer cell lines and one noncancerous cell were studied. The results revealed that some of conjugates exhibited better or comparable in vitro antitumor activity to 5-FU and emodin and low toxicity in the normal cell. The structure activity relationship study showed N-3-aromatic substituent was important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.050
• 作为产物：
  描述：

  大黄素 在 sodium dithionite 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.5h， 生成 1-羟基-2-(羟甲基)-6,8-二甲氧基-3-甲基蒽-9,10-二酮
  参考文献：
  名称：

  Synthesis and antitumor activity of conjugates of 5-Fluorouracil and emodin

  摘要：

  A series of conjugates of 5-Fluorouracil (5-FU) and emodin were synthesized by coupling trimethyl emodin with N-1, N-3 dialkylated 5-FU. The 5-FU moiety contained various substituents at the N-3-position were linked to the 2-position of trimethyl emodin via a methylene linkage. Their cytotoxicity against three cancer cell lines and one noncancerous cell were studied. The results revealed that some of conjugates exhibited better or comparable in vitro antitumor activity to 5-FU and emodin and low toxicity in the normal cell. The structure activity relationship study showed N-3-aromatic substituent was important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.050

文献信息

• An efficient regioselective synthesis of endocrocin and structural related natural anthraquinones starting from emodin
  作者：Mario Waser、Bernd Lackner、Joachim Zuschrader、Norbert Müller、Heinz Falk

  DOI：10.1016/j.tetlet.2005.02.061

  日期：2005.4

  Endocrocin and related naturally occurring anthraquinone pigments like cinnalutein could be synthesized regioselectively via a Marschalk type reaction, starting from the natural hydroxy anthraquinone emodin. Furthermore, the new tri-O-methyl protected emodin-2-carbaldehyde may serve as a promising synthon for new bathochromically shifted, higher generation photodynamically active hypericin derivatives. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• Synthesis and antitumor activity of conjugates of 5-Fluorouracil and emodin
  作者：Li-Ming Zhao、Li-Ming Zhang、Jin-Juan Liu、Li-Jing Wan、Yong-Qiang Chen、Shu-Qing Zhang、Zhi-Wei Yan、Ji-Hong Jiang

  DOI：10.1016/j.ejmech.2011.10.050

  日期：2012.1

  A series of conjugates of 5-Fluorouracil (5-FU) and emodin were synthesized by coupling trimethyl emodin with N-1, N-3 dialkylated 5-FU. The 5-FU moiety contained various substituents at the N-3-position were linked to the 2-position of trimethyl emodin via a methylene linkage. Their cytotoxicity against three cancer cell lines and one noncancerous cell were studied. The results revealed that some of conjugates exhibited better or comparable in vitro antitumor activity to 5-FU and emodin and low toxicity in the normal cell. The structure activity relationship study showed N-3-aromatic substituent was important for their cytotoxic activity. (C) 2011 Elsevier Masson SAS. All rights reserved.