4,11-dimethoxyanthra[2,3-b]furan-5,10-dione | 1356541-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione
• 英文别名: 4,11-dimethoxynaphtho[2,3-f][1]benzofuran-5,10-dione
• CAS: 1356541-68-8
• 化学式: C₁₈H₁₂O₅
• 分子量: 308.29
• InChiKey: JMVGXRNEHCXVAD-UHFFFAOYSA-N

物化性质

• 沸点：
  515.3±50.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,11-dimethoxyanthra[2,3-b]furan-5,10-dione 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 以88%的产率得到4,11-dihydroxyanthra[2,3-b]furan-5,10-dione
  参考文献：
  名称：

  5,12-萘并苯醌10的杂环类似物*呋喃喹啉及其新衍生物的合成

  摘要：

  开发了一种合成蒽[2,3 - b ]呋喃-5,10-二酮衍生物的新方法。呋喃片段与蒽醌发色团的脱嵌反应的关键化合物是以前未知的水杨醛类似物1,4-二甲氧基-3-甲酰基-2-羟基蒽醌，我们已经通过Miller-Loudon-Schneider反应合成了类似物。使用一连串的转化链将其转化为目标4,11-二羟基蒽[2,3- b ]呋喃-5,10-二酮（呋喃喹啉）：起始甲酰基羟基蒽醌与溴乙酸酯的O-烷基化，环-碱存在下使3-甲氧基蒽醌-2-基乙酸酯脱水，将所得酯水解为4,11-二甲氧基-5,10-dioxo-5,10-二氢蒽[2,3- b所得的4,11-二甲氧基蒽[2,3 - b ]呋喃-5,10-二酮的]呋喃-2-羧酸及其脱羧和脱甲基。

  DOI：

  10.1007/s10593-012-0895-4
• 作为产物：
  描述：

  4,11-dimethoxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-carboxylic acid 在 copper chromite 作用下， 以 喹啉 为溶剂， 反应 0.67h， 以5%的产率得到4,11-dimethoxyanthra[2,3-b]furan-5,10-dione
  参考文献：
  名称：

  Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione

  摘要：

  A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-halo-anthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

  DOI：

  10.1007/s10593-013-1240-2

文献信息

• Heterocyclic analogs of 5,12-naphtacenequinone 13*. Synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-diones and sulfur-containing analogs
  作者：Alexander S. Tikhomirov、Eugeny E. Bykov、Yury N. Luzikov、Alexander M. Korolev、Andrey E. Shchekotikhin

  DOI：10.1007/s10593-016-1968-6

  日期：2016.10

  We have developed an effective method for the synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-dione and 4,11-diaminoanthra[2,3-b]-thiophene-5,10-dione derivatives based on the substitution of 4,11-alkoxy groups with n-butylamine and subsequent oxidative dealkylation of n-butylamino groups via treatment with tetrabutylammonium hydroxide in DMSO.

  我们已经开发出一种合成4,11-二氨基蒽[2,3- b ]呋喃-5,10-二酮和4,11-二氨基蒽[2,3 - b ]-噻吩-5,10-二酮的有效方法衍生物是基于用正丁胺取代4,11-烷氧基，然后通过在DMSO中用氢氧化四丁铵处理正丁氨基的氧化脱烷基而得到的衍生物。
• Synthesis and Characterization of 4,11-Diaminoanthra[2,3-<i>b</i>]furan-5,10-diones: Tumor Cell Apoptosis through tNOX-Modulated NAD⁺/NADH Ratio and SIRT1
  作者：Alexander S. Tikhomirov、Andrey E. Shchekotikhin、Yi-Hui Lee、Yi-Ann Chen、Chia-An Yeh、Victor V. Tatarskiy、Lyubov G. Dezhenkova、Valeria A. Glazunova、Jan Balzarini、Alexander A. Shtil、Maria N. Preobrazhenskaya、Pin Ju Chueh

  DOI：10.1021/acs.jmedchem.5b00859

  日期：2015.12.24

  A series of new 4,11-diaminoanthra[2,3-b]furan-5,10-dione derivatives with different-side chains were synthesized. Selected 2-unsubstituted derivatives 11-14 showed: high antiproliferative potency on a panel of mammalian tumor cell lines including, multidrug resistance variants. Compounds 11-14 utilized multiple mechanisms of cytotoxicity including inhibition of Top1/Top2-mediated DNA relaxation, reduced NAD(+)/NADH ratio through tNOX inhibition, suppression of a NAD(+)-dependent sirtuin 1 (SIRT1) deacetylase activity, and activation of caspase-mediated apoptosis. Here, for the first time, we report that tumor-associated NADH oxidase (tNQX) and SIRT1 are important cellular targets of antitumor anthracene-9,10-dioties.