2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate | 29836-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate
• 英文别名: 2-(1-hydroxy-6-oxocyclohex-2-enecarbonyloxymethyl)phenyl 2-O-benzoyl-β-D-glucopyranoside；2'-benzoylsalicortin；tremulacin；Tremulaoin；[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl)oxymethyl]phenoxy]oxan-3-yl] benzoate
• CAS: 29836-40-6
• 化学式: C₂₇H₂₈O₁₁
• 分子量: 528.513
• InChiKey: RCKCYCDBDYUIGM-LFMHJWGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  11

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38

制备方法与用途

银耳霉素是一种重要的葡萄糖苷成分，存在于多种杨树的树皮和叶子中。

反应信息

• 作为反应物：
  描述：

  2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以46%的产率得到水杨苷
  参考文献：
  名称：

  Isolation of Salicin Derivatives from Homalium cochinchinensis and Their Antiviral Activities

  摘要：

  The chemical constituents of Homalium cochinchinensis were examined. From the root bark, in addition to the previously reported cochinolide and its beta-glucopyranoside, cochinchiside A (1) and tremulacinol (4) were isolated together with three known compounds [benzoic acid, tremulacin (2), and tremuloidin (3)]. From the leaves, cochinchiside B (5) was isolated as new compound. The structures of the new compounds (1, 4, 5) were determined by spectroscopic and/or chemical methods. Antiviral testing of compounds 2-5 against HSV-1 and HSV-2 showed that tremulacin (2) and cochinchiside B (5) were weakly active. Tremulacin (2) was also weakly active against HIV-1.

  DOI：

  10.1021/np034052o

文献信息

• [EN] DERIVATIVES COMPRISING STEROLS AND/OR STANOLS AND SPECIFIC CLASSES OF ANTI-INFLAMMATORY AGENTS AND USE THEREOF IN TREATING OR PREVENTING CARDIOVASCULAR DISEASE<br/>[FR] DERIVES COMPRENANT DES STEROLS ET/OU DES STANOLS ET DES CLASSES SPECIFIQUES D'AGENTS ANTI-INFLAMMATOIRES, ET UTILISATION DESDITS DERIVES POUR LE TRAITEMENT OU LA PREVENTION DE MALADIES CARDIOVASCULAIRES
  申请人：FORBES MEDI TECH INC

  公开号：WO2004029068A1

  公开（公告）日：2004-04-08

  The present invention provides, in one aspect, novel derivatives comprising sterols and/or stanols and an NSAID selected from salicylic acids and arylalkanoic acids, including salts of these derivatives, and having one or more of the following formulae: a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) formula (I), wherein R is a sterol or stanol moiety, R2 is derived from a salicylic acid or an arylalkanoic acid and n=1-5. Also provided are pharmaceutical compositions comprising one or more of these novel derivatives and methods of treating or preventing cardiovascular disease and its underlying conditions including, without limitation, atherosclerosis, hypercholesterolemia, hyperlipidemia, hypertension, thrombosis, coronary artery disease, and for treating and reducing inflammation including coronary plaque inflammation, bacterial-induced inflammation, viral induced inflammation and inflammation associated with acute pain and surgical procedures which comprises administering to an animal, particularly a human, a non-toxic and therapeutically effective amount of one or more of these compounds or a biologically acceptable salt thereof.

  本发明一方面提供了新颖的衍生物，包括甾醇和/或甾烷醇以及从水杨酸和芳烷酸中选择的非甾体抗炎药（NSAID），包括这些衍生物的盐，并具有以下一种或多种公式：a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) 公式 (I)，其中R是甾醇或甾烷醇部分，R2来自水杨酸或芳烷酸，n=1-5。还提供了包含一种或多种这些新颖衍生物的药物组合物，以及治疗或预防心血管疾病及其基础条件的方法，包括但不限于动脉粥样硬化、高胆固醇血症、高脂血症、高血压、血栓形成、冠心病，以及治疗和减少炎症的方法，包括冠状动脉斑块炎症、细菌诱导的炎症、病毒诱导的炎症以及与急性疼痛和手术程序相关的炎症，该方法包括向动物，尤其是人类，投予一种或多种这些化合物或其生物学可接受的盐的非毒性和治疗有效量。
• Novel structures and compositions comprising sterols and/or stanols and specific classes of anti-inflammatory agents and use thereof in treating or preventing cardiovascular disease, its underlying conditions including hyperlipidemia and other disorders having inflammation as part of their aetiology or presentation
  申请人：FORBES MEDI-TECH INC.

  公开号：US20040236125A1

  公开（公告）日：2004-11-25

  The present invention provides, in one aspect, novel derivatives comprising sterols and/or stanols and an NSAID selected from salicylic acids and arylalkanoic acids, including salts of these derivatives, and having one or more of the following formulae: 1 wherein R is a sterol or stanol moiety, R 2 is derived from a salicylic acid or an arylalkanoic acid and n=1-5. Also provided are pharmaceutical compositions comprising one or more of these novel derivatives and methods of treating or preventing cardiovascular disease and its underlying conditions including, without limitation, atherosclerosis, hypercholesterolemia, hyperlipidemia, hypertension, thrombosis, coronary artery disease, and for treating and reducing inflammation including coronary plaque inflammation, bacterial-induced inflammation, viral induced inflammation and inflammation associated with acute pain and surgical procedures which comprises administering to an animal, particularly a human, a non-toxic and therapeutically effective amount of one or more of these compounds or a biologically acceptable salt thereof.

  本发明提供了一种新的衍生物，包括甾醇和/或甾酚以及从水杨酸和芳基烷基酸中选择的NSAID，包括这些衍生物的盐，并具有以下一个或多个式子中的一个：1其中R是甾醇或甾酚基团，R2是从水杨酸或芳基烷基酸中派生的，n = 1-5。还提供了包括这些新的衍生物中的一个或多个的制药组合物以及治疗或预防心血管疾病及其基础病症的方法，包括但不限于动脉粥样硬化，高胆固醇血症，高脂血症，高血压，血栓形成，冠状动脉疾病，并用于治疗和减轻与急性疼痛和手术程序相关的炎症，包括冠状动脉斑块炎症，细菌感染引起的炎症，病毒感染引起的炎症和与之相关的炎症，其中包括向动物，特别是人类，给予这些化合物或其生物可接受的盐的非毒性和治疗有效量的方法。
• Verwendung von Wirkstoffgemischen zur Herstellung eines Medikamentes gegen rheumatische Arthritis
  申请人：Cognis Iberia, S.L.

  公开号：EP1374882A1

  公开（公告）日：2004-01-02

  Vorgeschlagen wird die Verwendung von Mischungen, enthaltend (a) Tocopherole und (b) Extrakte von Pflanzen der Familie Salix bzw. deren Wirkstoffe, ausgewählt aus der Gruppe, die gebildet wird von Salicin, Salicortin und Tremulacin, zur Herstellung eines Medikamentes gegen rheumatische Arthritis.

  建议使用含有以下成分的混合物 (a) 生育酚和 (b) 柳科植物萃取物或其活性成分，这些活性成分选自柳叶素、柳叶素和透骨草 素、 用于制造防治类风湿性关节炎的药物。
• Mikrokapseln (XXX), enthaltend Pflanzenextrakte, und Verfahren zu deren Herstellung
  申请人：Cognis IP Management GmbH

  公开号：EP1602364A1

  公开（公告）日：2005-12-07

  Vorgeschlagen werden Mikrokapseln mit mittleren Durchmessern im Bereich von 0,0001 bis 5 mm, die dadurch erhältlich sind , dass man (a) wässrige Zubereitungen von Polymeren, die erst bei pH-Werten oberhalb von 5,5 löslich sind auf einen alkalischen pH-Wert einstellt, (b) die so erhaltenen Lösungen mit Pflanzenextrakten vermischt und (c) die Zubereitungen einer Sprühtrocknung unterwirft.

  提出了平均直径在 0.0001 至 5 毫米范围内的微胶囊，可通过以下方法获得 (a) 将聚合物的水溶液（只溶于 5.5 以上的 pH 值）调至碱性 pH 值、 (b) 将由此获得的溶液与植物提取物混合，以及 (c) 将制剂喷雾干燥。
• Active compositions comprising lycopene, cytidin and fatty acids
  申请人：Cognis IP Management GmbH

  公开号：EP1618800A1

  公开（公告）日：2006-01-25

  Suggested are active compositions, comprising (a) extracts of tomatoes or their active principles, and (b) physiologically active fatty acids, their salts or their esters.

  建议的活性成分包括 (a) 西红柿提取物或其活性成分，以及 (b) 具有生理活性的脂肪酸、其盐类或酯类。