消退素E2 | 865532-70-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 消退素E2
• 中文别名: 二十碳五烯酸杂质16
• 英文名称: (5S,6E,8Z,11Z,14Z,16E,18R)-5,18-dihydroxy-6,8,11,14,16-eicosapentaenoic acid
• 英文别名: (5S,6E,8Z,11Z,14Z,16E,18R)-5,18-dihydroxyicosa-6,8,11,14,16-pentaenoic acid；resolvin E2；5S,18R dihydroxy-EPE；5S,18-RdiHEPE
• CAS: 865532-70-3
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: KPRHYAOSTOHNQA-NNQKPOSRSA-N

物化性质

• 溶解度：
  乙醇：1 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(三甲基硅烷基)-1-戊炔-3-酮 在 咪唑 、 甲醇 、 正丙胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 [N-[(1S,2S)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium formate 、 十六烷基三甲基溴化铵 、 silver nitrate 、 乙酰氯 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 16.0h， 生成 消退素E2
  参考文献：
  名称：

  抗炎脂质介体Resolvin E2的全合成

  摘要：

  已经实现了Resolvin E2的全合成，Resolvin E2是一种可解决二十碳五烯酸的炎症的内源性脂质介质。通过使用甲酸钠作为还原剂在水中进行不对称的Noyori转移加氢，以简单，有效和环保的方式生成C5和C18处的手性羟基。三个关键片段的Pd 0 / Cu I Sonogashira偶联和Zn（Cu / Ag）还原完成了Resolvin E2的合成。

  DOI：

  10.1016/j.tetlet.2012.01.136

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT D'UNE INFLAMMATION
  申请人：RESOLVYX PHARMACEUTICALS INC

  公开号：WO2010120719A1

  公开（公告）日：2010-10-21

  The invention relates to novel resolvin compounds and pharmaceutical preparations thereof. The invention further relates to methods of treatment using the novel resolvin compounds of the invention.

  这项发明涉及新型利用新型resolvin化合物和其药物制剂的治疗方法。
• [EN] COMPOSITIONS AND METHODS FOR ORGAN PRESERVATION<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE CONSERVATION D'ORGANE
  申请人：RESOLVYX PHARMACEUTICALS INC

  公开号：WO2010091226A1

  公开（公告）日：2010-08-12

  The invention relates to reducing, preventing or reversing organ damage, reducing and/or preventing stem cell damage and/or death, enhancing organ preservation and/or survival, or enhancing stem cell preservation and/or survival comprising administering a compound of formula A, a compound of any one of formulae 1-49 or I-III, a lipoxin compound, an oxylipin compound, or a combination of aspirin and an omega-3 fatty acid.

  该发明涉及减少、预防或逆转器官损伤，减少和/或预防干细胞损伤和/或死亡，增强器官保存和/或存活，或增强干细胞保存和/或存活的方法，包括给予化合物A的化合物，任何一个化合物1-49或I-III的化合物，脂氧合素化合物，氧脂素化合物，或阿司匹林和ω-3脂肪酸的组合。
• Design and Synthesis of Cyclopropane Congeners of Resolvin E2, an Endogenous Proresolving Lipid Mediator, as Its Stable Equivalents
  作者：Hayato Fukuda、Ryuta Muromoto、Yuuki Takakura、Kohei Ishimura、Ryutaro Kanada、Daichi Fushihara、Makoto Tanabe、Kotaro Matsubara、Toru Hirao、Koki Hirashima、Hiroshi Abe、Mitsuhiro Arisawa、Tadashi Matsuda、Satoshi Shuto

  DOI：10.1021/acs.orglett.6b02612

  日期：2016.12.16

  are unstable in oxygen due to their characteristic polyunsaturated structures. To solve the problem, CP-RvE2 has been designed and synthesized in which the cis-olefin of RvE2 was replaced with a cyclopropane. CP-RvE2s were much more stable than RvE2 against autoxidation and equipotent or more potent than RvE2. CP-RvE2s were successfully identified as stable equivalents of RvE2.

  具有强效抗炎活性的脂类化学介质可分辨酚可以开发出新型的抗炎药。然而，由于其特有的多不饱和结构，它们在氧气中不稳定。为了解决该问题，已经设计并合成了CP-RvE2，其中用环丙烷代替了RvE2的顺式烯烃。CP-RvE2的抗自氧化能力比RvE2稳定得多，并且与RvE2相比具有更强的效价。CP-RvE2已成功鉴定为RvE2的稳定等同物。
• Resolvins: Biotemplates for therapeutic interventions
  申请人：BRIGHAM AND WOMEN'S HOSPITAL

  公开号：EP2216318A2

  公开（公告）日：2010-08-11

  The present invention is generally drawn to novel isolated therapeutic agents, termed resolvins, generated from the interaction between a dietary omega-3 polyunsaturated fatty acid (PUFA) such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA), cyclooxygenase-II (COX-2) and an analgesic, such as aspirin (ASA). Surprisingly, careful isolation of compounds generated from the combination of components in an appropriate environment provide di- and tri-hydroxy EPA or DHA compounds having unique structural and physiological properties. The present invention therefore provides for many new useful therapeutic di- or tri-hydroxy derivatives of EPA or DHA (resolvins) that diminish, prevent, or eliminate inflammation or PMN migration, for example. The present invention also provides methods of use, methods of preparation, and packaged pharmaceuticals for use as medicaments for the compounds disclosed throughout the specification.

  本发明一般涉及新型分离治疗剂，称为 resolvins，由膳食中的ω-3 多不饱和脂肪酸（PUFA）如二十碳五烯酸（EPA）或二十二碳六烯酸（DHA）、环氧化酶-II（COX-2）和镇痛剂如阿司匹林（ASA）之间的相互作用产生。令人惊奇的是，在适当的环境中仔细分离由各种成分组合产生的化合物，可以得到具有独特结构和生理特性的二羟基和三羟基 EPA 或 DHA 化合物。因此，本发明提供了许多新的有用的 EPA 或 DHA 的二羟基或三羟基治疗性衍生物（resolvins），这些衍生物可减轻、预防或消除炎症或 PMN 迁移等。本发明还提供了整个说明书中公开的化合物的使用方法、制备方法和用作药物的包装药品。
• NOVEL ANTI-INFLAMMATORY METABOLITE DERIVED FROM OMEGA-3-TYPE FATTY ACID
  申请人：The University of Tokyo

  公开号：EP2607358A1

  公开（公告）日：2013-06-26

  The purpose is to provide a compound which can overcomes the disadvantages of conventional steroid drugs and NSAID. It is found that specific epoxy monohydroxy forms of eicosapentaenoic acid, d ocosahexaenoic acid and docosapentaenoic acid which are independently represented by formulae [chemical formula 1], [chemical formula 5] and the like have an inhibitory activity on neutrophils. This compound can inhibit the invasion of neutrophils into tissues and the activation of neutrophils which are observed in acute inflammations.

  目的是提供一种能克服传统类固醇药物和非甾体抗炎药缺点的化合物。研究发现，由式[化学式 1]、[化学式 5]等独立表示的二十碳五烯酸、二十二碳六烯酸和二十二碳五烯酸的特定环氧单羟基形式对中性粒细胞具有抑制活性。这种化合物可抑制中性粒细胞侵入组织和中性粒细胞的活化，这在急性炎症中是可以观察到的。