3,4-dihydroxy-5-[2-(1-naphthoxy)ethyl]-2(5H)-furanone | 203863-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,4-dihydroxy-5-[2-(1-naphthoxy)ethyl]-2(5H)-furanone
• 英文别名: 3,4-dihydroxy-2-(2-naphthalen-1-yloxyethyl)-2H-furan-5-one
• CAS: 203863-47-2
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: XMBUVAMZXSWJNF-UHFFFAOYSA-N

物化性质

• 沸点：
  541.5±50.0 °C(predicted)
• 密度：
  1.434±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  萘酚 、 3,4-bis(benzyloxy)-5-(2-hydroxyethyl)furan-2(5H)-one 以26%的产率得到3,4-dihydroxy-5-[2-(1-naphthoxy)ethyl]-2(5H)-furanone
  参考文献：
  名称：

  5,5-Disubstituted-3, 4-dihydroxy-2(5H)-furanones and methods of use

  摘要：

  本发明涉及用于合成旋光活性和消旋5,5-二取代-3,4-二羟基-2(5H)-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2(5H)-呋喃酮；5-(2-芳硫基)乙基-3,4-二羟基-2(5H)-呋喃酮；以及5-(2-芳氧基)乙基-3,4-二羟基-2(5H)-呋喃酮的生产的合成方法。本发明进一步涉及上述化合物作为抗炎药物的用途，通过它们作为脂质过氧化、5-脂氧合酶、环氧合酶-1和环氧合酶-2的混合抑制剂的作用。该发明还涉及将这些化合物用于治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征，以及阿尔茨海默病和帕金森病等中枢神经系统疾病，其中活性氧自由基和炎症介质是造成有害因素的。

  公开号：

  US06005000A1

文献信息

• Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
  申请人：——

  公开号：US20030065196A1

  公开（公告）日：2003-04-03

  This invention affords a solution to the technical problem of obtaining one or both enantiomers of 5-substituted 4-hydroxyfuran-2-ones in pure form by resolution with enantiomerically pure bases. Racemic mixtures of 5-substituted 4-hydroxy-2(5H)-furanones, including 5-substituted and 5,5-disubstituted, 4-hydroxy and 3,4-dihydroxy furanones are separated into pure enantiomers by crystallization with an enantiomerically pure base, such as cinchonidine. In specific solvent mixtures, for example, 95% ethanol, the diastereomerically pure salt of one enantiomer crystallizes. The enantiomerically pure furanone can then be obtained simply by filtration and treatment of the salt with an acid, for example, trifluoracetic acid, followed by precipitation with water, filtration and drying. Moreover, the other enantiomer may be equally obtained in pure form by evaporation of the mother liquor, followed by the same treatment of the salt as described before.

  本发明提供了一种解决技术问题的方法，即通过与对映纯基团分离得到5-取代4-羟基呋喃-2-酮的一个或两个对映体。包括5-取代和5,5-二取代，4-羟基和3,4-二羟基呋喃酮的混合物被晶化与对映纯碱，例如金鸡纳碱，分离成纯对映体。在特定的溶剂混合物中，例如95%的乙醇，一个对映异构体纯盐结晶。然后可以通过过滤和用酸处理盐，例如三氟乙酸，随后用水沉淀，过滤和干燥来获得对映纯呋喃酮。此外，通过蒸发母液，然后用与之前相同的方法处理盐，同样可以获得另一个对映体的纯形式。
• Pharmaceutical methods of use of 5-substituted and 5,5 disubstituted-3,4-dihydroxy-2(5H)-furanones
  申请人：Oxis International Inc.

  公开号：US06262073B1

  公开（公告）日：2001-07-17

  The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

  本发明涉及合成方法，用于生产旋光和消旋5,5-二取代-3,4-二羟基-2（5H）-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2（5H）-呋喃酮；5-（2-芳硫基）乙基-3,4-二羟基-2（5H）-呋喃酮；以及5-（2-芳氧基）乙基-3,4-二羟基-2（5H）-呋喃酮。本发明进一步涉及上述化合物的用途，作为抗炎剂，通过它们作为脂质过氧化、5-脂氧合酶、环氧化酶-1和环氧化酶-2的混合抑制剂的作用。本发明进一步涉及在治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征和中枢神经系统疾病，如阿尔茨海默病和帕金森病中使用这些化合物，其中活性氧物质和炎症介质是造成有害因素的贡献者。
• 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones and methods of use
  申请人：Oxis International Inc.

  公开号：US06136832A1

  公开（公告）日：2000-10-24

  The present invention relates to synthetic methods for the production of both optically active and racemic 5,5-disubstituted-3,4-dihydroxy-2(5H)-furanones; 5-[(4-aryl)-3-butynyl]-3,4-dihydroxy-2(5H)-furanones; 5-(2-arylthio)ethyl-3,4-dihydroxy-2(5H)-furanones; and 5-(2-aryloxy)ethyl-3,4-dihydroxy-2(5H)-furanones. This invention further relates to the use of the above mentioned compounds as anti-inflammatory agents through their action as mixed inhibitors of lipid peroxidation, 5-lipoxygenase, cyclooxygenase-1 and cyclooxygenase-2. The invention further relates to the use of such compounds in the treatment of chronic inflammatory disorders such as asthma, rheumatoid arthritis, inflammatory bowel disease, atherosclerosis, acute respiratory distress syndrome, and central nervous system disorders such as Alzheimer's and Parkinson's disease wherein reactive oxygen species and inflammatory mediators are contributing deleterious factors.

  本发明涉及合成方法，用于生产旋光和消旋5,5-二取代-3,4-二羟基-2（5H）-呋喃酮；5-[(4-芳基)-3-丁炔基]-3,4-二羟基-2（5H）-呋喃酮；5-（2-芳硫基）乙基-3,4-二羟基-2（5H）-呋喃酮；以及5-（2-芳氧基）乙基-3,4-二羟基-2（5H）-呋喃酮。本发明还涉及上述化合物作为抗炎药物的用途，通过它们作为脂质过氧化、5-脂氧合酶、环氧合酶-1和环氧合酶-2的混合抑制剂的作用。本发明还涉及在治疗慢性炎症性疾病，如哮喘、类风湿性关节炎、炎症性肠病、动脉粥样硬化、急性呼吸窘迫综合征以及中枢神经系统疾病，如阿尔茨海默病和帕金森病等，其中活性氧和炎症介质是致病因素的情况下使用这些化合物的用途。
• 5-SUBSTITUTED AND 5,5-DISUBSTITUTED-3,4-DIHYDROXY-2(5H)-FURANONES AND METHODS OF USE THEREFOR
  申请人：Oxis International, Inc.

  公开号：EP0938482A1

  公开（公告）日：1999-09-01
• METHODS FOR RESOLVING RACEMIC MIXTURES OF 5-SUBSTITUTED 4-HYDROXY-2-FURANONES
  申请人：OXIS Isle of Man, Limited

  公开号：EP1246811B1

  公开（公告）日：2003-12-03