1-[2-(5-Carboxy-4-hydroxy-pentanoyl)-6-hydroxy-benzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid | 252961-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-[2-(5-Carboxy-4-hydroxy-pentanoyl)-6-hydroxy-benzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid
• 英文别名: Mumbaistatin；1-[2-(5-carboxy-4-hydroxypentanoyl)-6-hydroxybenzoyl]-3,8-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
• CAS: 252961-22-1
• 化学式: C₂₈H₂₀O₁₂
• 分子量: 548.46
• InChiKey: XFESZXMDORIFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  224
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 1-[2-(5-Carboxy-4-hydroxy-pentanoyl)-6-hydroxy-benzoyl]-3,8-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 以 甲醇 为溶剂， 以2 mg的产率得到
  参考文献：
  名称：

  The Chemical Structure of Mumbaistatin, a Novel Glucose-6-phosphate Translocase Inhibitor Produced by Streptomyces sp. DSM 11641.

  摘要：

  The characterization of the structure of mumbaistatin (1), an effective inhibitor of the glucose-6-phosphatase system (EC 3.1.3.9), is reported. Isolation of mumbaistatin from cultures of Streptomyces sp. DSM 11641 was achieved by anion-exchange and reversed-phase chromatography. The acid-labile inhibitor was methylated for the structure determination. Single-crystal X-ray structure analysis of a triply methylated dehydration product, C31H24O11, revealed the structure of an aromatic dispirodiketal (2), a compound containing a previously undescribed ring system. Extensive 2D-NMR experiments with mumbaistatin and with the methylation products showed that mumbaistatin itself possesses the hydroxydiketodicarboxylic acid structure 1, C28H20O12, which, in the presence of acid or upon activation through methyl ester formation, undergoes self-condensation with loss of water to the dispirodiketal form (2). Mumbaistatin is an anthraquinone derivative, whose open-chain diketo form acts as a specific and powerful inhibitor of glucose-6-phosphate translocase: IC50=5nM. The activity towards the same enzyme of the cyclized dispirodiketal derivatives is roughly one thousand times lower.

  DOI：

  10.7164/antibiotics.54.354

文献信息

• METHOD FOR THE PRODUCTION OF MUMBAISTATIN DERIVATIVES
  申请人：SCHWINK Lothar

  公开号：US20090156836A1

  公开（公告）日：2009-06-18

  The present invention relates to a process for preparing mumbaistatin derivatives (I), where the anthraquinone skeleton is constructed via a Diels-Alder reaction and the central methylene bridge via a transition metal-catalyzed reaction, and to the intermediates used in this process.

  本发明涉及一种制备孟买斯塔汀衍生物（I）的方法，其中蒽醌骨架通过Diels-Alder反应构建，中央亚甲基桥通过过渡金属催化反应构建，并涉及用于该过程的中间体。
• US7763740B2
  申请人：——

  公开号：US7763740B2

  公开（公告）日：2010-07-27
• [DE] VERFAHREN ZUR HERSTELLUNG VON MUMBAISTATIN-DERIVATEN<br/>[EN] METHOD FOR THE PRODUCTION OF MUMBAISTATIN DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS DE MUMBAISTATINE
  申请人：SANOFI AVENTIS

  公开号：WO2007121822A1

  公开（公告）日：2007-11-01

  [EN] The current invention relates to a production method for mumbaistatin derivatives (I), wherein the basic framework of the anthraquinone is built up by means of a Diels-Alder reaction and the central methylene bridge is built up by means of a transitional metal catalyzed reaction, and to the intermediates used in this method.
  [FR] La présente invention concerne un procédé de production de dérivés de mumbaistatine (I), dans lequel la structure de base anthraquinone est construite sur une réaction de Diels-Alder et le pont méthylène central, sur une réaction catalysée par un métal de transition, et les intermédiaires utilisés dans ce procédé.
  [DE] Die vorliegende Erfindung betrifft ein Herstellungsverfahren für Mumbaistatin-Derivate (I), wobei das Anthrachinon-Grundgerüst über eine Diels-Alder-Reaktion und die zentrale Methylenbrücke über eine Übergangsmetall-katalysierte Reaktion aufgebaut wird, sowie die in diesem Verfahren verwendeten Intermediate.