5-[(E)-2-carboxyvinyl]-7-hydroxy-2β-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3α-carboxylic acid | 884843-14-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-[(E)-2-carboxyvinyl]-7-hydroxy-2β-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3α-carboxylic acid
• 英文别名: 5-[(E)-2-carboxyethenyl]-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3-carboxylic acid
• CAS: 884843-14-5
• 化学式: C₁₉H₁₆O₈
• 分子量: 372.331
• InChiKey: SFGXKKAKESQTQX-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (E)-3-[2β-(4-hydroxy-3-methoxyphenyl)-7-hydroxy-3α-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl] prop-2-enoate 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-[(E)-2-carboxyvinyl]-7-hydroxy-2β-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzofuran-3α-carboxylic acid
  参考文献：
  名称：

  NOVEL CHEMOTHERAPEUTIC AGENTS AGAINST INFLAMMATION AND CANCER

  摘要：

  提供了新型化合物、其制备方法以及在与癌症和炎症相关的治疗中的用途。这些化合物包括肉桂酸酯、香草酸酯和4-羟基肉桂酸酯及其衍生物和盐。提供了具有新型苯并呋喃木脂素结构的化合物，作为一种强效抗有丝分裂剂和诱导凋亡剂。还提供了用于治疗NF-kappaB介导的疾病的配方和方法。

  公开号：

  US20100168228A1

文献信息

• Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Cross-coupling and dimerization reactions
  作者：D ARRIETABAEZ、R STARK

  DOI：10.1016/j.phytochem.2006.01.026

  日期：2006.4

  An anionic potato peroxidase (EC 1.11.1.7, APP) thought to be involved in suberization after wounding was isolated from slices of Solanum tuberosum in order to elucidate the first steps of dehydrogenative polymerization between pairs of different hydroxycinnamic acids (FA, CafA, CA and SA) present in wound-healing plant tissues. Use of a commercial horseradish peroxidase (HRP)-H2O2 catalytic system gave the identical major products in these coupling reactions, providing sufficient quantities for purification and structural elucidation. Using an equimolar mixture of pairs of hydroxycinnamic acid suberin precursors, only caffeic acid is coupled to ferulic acid and sinapic acid in separate cross-coupling reactions. For the other systems, HRP and APP reacted as follows: (1) preferentially with ferulic acid in a reaction mixture that contained p-coumaric and ferulic acids; (2) with sinapic acid in a mixture of p-coumaric and sinapic acids; (3) with sinapic acid in a mixture of ferulic and sinapic acids; (4) with caffeic acid in a reaction mixture of p-coumaric and caffeic acids. The resulting products, isolated and identified by NMR and MS analysis, had predominantly beta-beta-gamma-lactone and beta-5 benzofuran molecular frameworks. Five cross-coupling products are described for the first time, whereas the beta-O-4 dehydrodimers identified from the caffeic acid and sinapic acid cross-coupling reaction are known materials that are highly abundant in plants. These reactivity trends lead to testable hypotheses regarding the molecular architecture of intractable suberin protective plant materials, complementing prior analysis of monomeric constituents by GC-MS and polymer functional group identification from solid-state NMR, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• CINNAMIC ACID, VANILLIC ACID AND BENZOFURAN DERIVATIVES FOR USE IN THE TREATMENT OF INFLAMMATION AND CANCER
  申请人：Reliance Life Sciences Pvt., Ltd.

  公开号：EP2081565A2

  公开（公告）日：2009-07-29
• [EN] NOVEL CHEMOTHERAPEUTIC AGENTS AGAINST INFLAMMATION AND CANCER<br/>[FR] NOUVEAUX AGENTS CHIMIOTHÉRAPEUTIQUES CONTRE L'INFLAMMATION ET LE CANCER
  申请人：RELIANCE LIFE SCIENCES PVT LTD

  公开号：WO2008062466A2

  公开（公告）日：2008-05-29

  [EN] Novel compounds, their methods of preparation and use in therapies related to cancer and inflammation are provided. Compounds comprise esters of cinnamic acid, vanillic acid and 4- hyrdoxy cinnamic acid and derivatives and salts thereof. Compounds with novel benzofuran lignan structure as a potent antimitotic agent and inducer of apoptosis are provided. Formulations and methods for treatment of diseases mediated by NF-kappaB are also provided.
  [FR] L'invention concerne de nouveaux composés, leurs procédés de préparation et leur utilisation dans des traitements associés au cancer et à l'inflammation. Lesdits composés comprennent des esters d'acide cinnamique, d'acide vanillique et d'acide 4-hydroxy-cinnamique ainsi que des dérivés et des sels correspondants. L'invention concerne également des composés présentant une nouvelle structure benzofurane lignane, utilisés comme puissant agent antimitotique et comme puissant inducteur de l'apoptose. L'invention se rapporte en outre à des préparations et des méthodes de traitement de maladies médiées par le NF-kappaB.