8-Hydroxy-3-methoxy-1-methylanthrachinon-2-carbonsaeure-methylester | 53254-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8-Hydroxy-3-methoxy-1-methylanthrachinon-2-carbonsaeure-methylester
• 英文别名: methyl 8-hydroxy-3-methoxy-1-methylanthraquinone-2-carboxylate；Aloesaponarin I 3-methylether；aloesaponarin I 6-methyl ether；8-hydoxy-3-methoxy-1-methylanthraquinone-2-carboxylic acid methyl ester；8-Hydroxy-3-methoxy-2-methoxycarbonyl-1-methylanthrachinon；3,8-Dihydroxy-1-methyl-anthraquinone-2-carboxylic acid；methyl 8-hydroxy-3-methoxy-1-methyl-9,10-dioxoanthracene-2-carboxylate
• CAS: 53254-91-4
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: BDCYFLNKHCNXDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-Hydroxy-3-methoxy-1-methylanthrachinon-2-carbonsaeure-methylester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以80%的产率得到
  参考文献：
  名称：

  Structure–activity relationships of semisynthetic mumbaistatin analogs

  摘要：

  Mumbaistatin (1), a new anthraquinone natural product, is one of the most potent known inhibitors of hepatic glucose-6-phosphate translocase, an important target for the treatment of type II diabetes. Its availability, however, has been limited due to its extremely low yield from the natural source. Starting from DMAC (5, 3,8-dihydroxyanthraquinone-2-carboxylic acid), a structurally related polyketide product of engineered biosynthesis, we developed a facile semisynthetic method that afforded a variety of mumbaistatin analogs within five steps. This work was facilitated by the initial development of a DMAC overproduction system. In addition to reinforcing the biological significance of the anthraquinone moiety of mumbaistatin, several semisynthetic analogs were found to have low micromolar potency against the translocase in vitro. Two of them were also active in glucose release assays from primary hepatocytes. The synergistic combination of biosynthesis and synthesis is a promising avenue for the discovery of new bioactive substances. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.019
• 作为产物：
  描述：

  2-acetyl-3-methoxy-but-2-enoic acid methyl ester 以 乙醚 、 苯 为溶剂， 反应 84.0h， 生成 8-Hydroxy-3-methoxy-1-methylanthrachinon-2-carbonsaeure-methylester
  参考文献：
  名称：

  Cameron, Donald W.; Deutscher, D. Jeanne; Feutrill, Geoffrey I., Australian Journal of Chemistry, 1981, vol. 34, # 11, p. 2401 - 2421

  摘要：

  DOI：

文献信息

• An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.
  作者：Brigitte Caron、Paul Brassard

  DOI：10.1016/s0040-4020(01)80322-7

  日期：1993.1

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.
• IMAGE FADING PREVENTING AGENT, IMAGE FORMING ELEMENT, RECORDING MEDIUM, IMAGE FORMING METHOD AND IMAGE
  申请人：Ishikawa Takayuki

  公开号：US20070093386A1

  公开（公告）日：2007-04-26

  The invention provides an image fading preventing agent capable of preventing the discoloration/fading of an image formed and stably retaining its image quality over a long period of time, as well as an image forming element, a recording medium, an image forming method and an image using the agent. The image fading preventing agent is used in a region in which an image is formed by a coloring material, and has a functional group to cause intramolecular proton transfer in its molecule. An image is formed by the image forming element, recording medium or image forming method using the agent.
• 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.
• US7737084B2
  申请人：——

  公开号：US7737084B2

  公开（公告）日：2010-06-15
• Structure–activity relationships of semisynthetic mumbaistatin analogs
  作者：Taek Soon Lee、Abhirup Das、Chaitan Khosla

  DOI：10.1016/j.bmc.2007.05.019

  日期：2007.8

  Mumbaistatin (1), a new anthraquinone natural product, is one of the most potent known inhibitors of hepatic glucose-6-phosphate translocase, an important target for the treatment of type II diabetes. Its availability, however, has been limited due to its extremely low yield from the natural source. Starting from DMAC (5, 3,8-dihydroxyanthraquinone-2-carboxylic acid), a structurally related polyketide product of engineered biosynthesis, we developed a facile semisynthetic method that afforded a variety of mumbaistatin analogs within five steps. This work was facilitated by the initial development of a DMAC overproduction system. In addition to reinforcing the biological significance of the anthraquinone moiety of mumbaistatin, several semisynthetic analogs were found to have low micromolar potency against the translocase in vitro. Two of them were also active in glucose release assays from primary hepatocytes. The synergistic combination of biosynthesis and synthesis is a promising avenue for the discovery of new bioactive substances. (c) 2007 Elsevier Ltd. All rights reserved.