4-phenyl-5-hydroxy-2-(5H)-furanone | 78920-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-phenyl-5-hydroxy-2-(5H)-furanone
• 英文别名: 4-phenyl-5-hydroxy-2(5H)-furanone；5-hydroxy-4-phenyl-2(5H)-furanone；5-hydroxy-4-phenyl-5H-furan-2-one；5-hydroxy-4-phenylbutenolide；5-hydroxy-4-phenylfuran-2(5H)-one；2-hydroxy-3-phenyl-2H-furan-5-one
• CAS: 78920-11-3
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: XXWIUGNNANJILR-UHFFFAOYSA-N

物化性质

• 熔点：
  158.0-158.8 °C(Solv: benzene (71-43-2))
• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-5-hydroxy-2-(5H)-furanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-苯基-2H-呋喃-5-酮
  参考文献：
  名称：

  Analogs of .gamma.-hydroxybutyric acid. Synthesis and binding studies

  摘要：

  Substituted 4-hydroxybutyric (GHB) or trans-4-hydroxycrotonic acids (T-HCA) and structurally related compounds were synthesized and submitted to [3H]GHB binding. Structure-activity relationships studies highlighted for [3H]GHB binding (a) the necessity of a nonlactonic, relatively extended conformation of the gamma-hydroxybutyric chain, (b) the existence of some bulk tolerance in the vicinity of the hydroxyl group, and (c) the high sensitivity toward isosteric replacements of the carboxyl or the hydroxyl groups. T-HCA has been recently identified as a naturally occurring substance in the central nervous system (CNS) and shows a better affinity than GHB. Our findings are in favor of the presence in the CNS of specific GHB binding sites, which are different from the GABA and the picrotoxin binding sites, and for which T-HCA may be an endogenous ligand.

  DOI：

  10.1021/jm00400a001
• 作为产物：
  描述：

  3-phenyl-4-ethoxy-2-butenolide 在 盐酸 作用下， 反应 0.25h， 生成 4-phenyl-5-hydroxy-2-(5H)-furanone
  参考文献：
  名称：

  Lactone chemistry. Synthesis of .beta.-substituted, .gamma.-functionalized butan- and butenolides and succinaldehydic acids from glyoxylic acid

  摘要：

  DOI：

  10.1021/jo00337a013

文献信息

• Regioselective Entry to Bromo-γ-hydroxybutenolides:  Useful Building Blocks for Assemblying Natural Product-Like Libraries
  作者：M. Aquino、I. Bruno、R. Riccio、L. Gomez-Paloma

  DOI：10.1021/ol0618611

  日期：2006.10.1

  [reaction: see text] We report a regioselective entry to 3-bromo- and 4-bromo-5-hydroxy-5H-furan-2-ones by photooxidation of 3-bromofuran with a singlet oxygen in the presence of a suitable base. By this procedure, a variety of 3-substituted gamma-hydroxybutenolides have become for the first time easily accessible. Strategies employing these highly functionalized building blocks for the preparation

  [反应：见正文]我们报告了在适当的碱存在下，通过3-溴呋喃与单线态氧的光氧化作用，可以选择性地3-溴和4-溴-5-羟基-5H-呋喃-2-酮的区域选择性进入。通过这种方法，各种3-取代的γ-羟基丁烯内酯首次变得容易获得。还讨论了使用这些高度功能化的构建基块来制备天然类分子聚焦库的策略。
• Synthesis and structure-activity relationships of a series of aminopyridazine derivatives of .gamma.-aminobutyric acid acting as selective GABA-A antagonists
  作者：Camille Georges Wermuth、Jean Jacques Bourguignon、Gilbert Schlewer、Jean Pierre Gies、Angele Schoenfelder、Anita Melikian、Marie Jeanne Bouchet、Dominique Chantreux、Jean Charles Molimard

  DOI：10.1021/jm00385a003

  日期：1987.2

  We have recently shown that an arylaminopyridazine derivative of GABA, SR 95103 [2-(3-carboxypropyl)-3-amino-4-methyl-6-phenylpyridazinium chloride], is a selective and competitive GABA-A receptor antagonist. In order to further explore the structural requirements for GABA receptor affinity, we synthesized a series of 38 compounds by attaching various pyridazinic structures to GABA or GABA-like side

  我们最近发现，GABA的芳基氨基哒嗪衍生物SR 95103 [2-（3-羧丙基）-3-氨基-4-甲基-6-苯基吡啶并鎓氯化物]是一种选择性和竞争性的GABA-A受体拮抗剂。为了进一步探索对GABA受体亲和力的结构要求，我们通过将各种哒嗪结构连接到GABA或GABA样侧链上，合成了38种化合物。大多数化合物从大鼠脑膜中取代了[3H] GABA。所有活性化合物都拮抗了GABA引起的[3H]地西p结合的增强，强烈表明所有这些化合物都是GABA-A受体拮抗剂。从大鼠脑膜置换[3H] GABA的化合物均未与其他GABA识别位点（GABA-B受体，GABA吸收结合位点，谷氨酸脱羧酶，GABA转氨酶）相互作用。它们不与与GABA-A受体相关的Cl-离子载体相互作用，也不与苯并二氮杂str，士的宁和谷氨酸结合位点相互作用。因此，这些化合物似乎是特异性的GABA-A受体拮抗剂。就结构活性而言，可以得出结论，
• Substituted heterocyclic compounds and methods of use
  申请人：Andersen Lyn Denise

  公开号：US20060069110A1

  公开（公告）日：2006-03-30

  The present invention relates to pyridines, pyrimidines and derivatives thereof, and pharmaceutically acceptable salts thereof. Also included is a method of treatment of inflammation, rheumatoid arthritis, Pagets disease, osteoporosis, multiple myeloma, uveititis, acute or chronic myelogenous leukemia, pancreatic β cell destruction, osteoarthritis, rheumatoid spondylitis, gouty arthritis, inflammatory bowel disease, adult respiratory distress syndrome (ARDS), psoriasis, Crohn's disease, allergic rhinitis, ulcerative colitis, anaphylaxis, contact dermatitis, asthma, muscle degeneration, cachexia, Reiter's syndrome, type I diabetes, type II diabetes, bone resorption diseases, graft vs. host reaction, Alzheimer's disease, stroke, myocardial infarction, ischemia reperfusion injury, atherosclerosis, brain trauma, multiple sclerosis, cerebral malaria, sepsis, septic shock, toxic shock syndrome, fever, myalgias due to HIV-1, HIV-2, HIV-3, cytomegalovirus (CMV), influenza, adenovirus, the herpes viruses or herpes zoster infection in a mammal comprising administering an effective amount a compound as described above.

  本发明涉及吡啶、嘧啶及其衍生物，以及其药用盐。还包括一种治疗炎症、类风湿关节炎、帕盖特病、骨质疏松症、多发性骨髓瘤、葡萄膜炎、急性或慢性骨髓性白血病、胰岛素β细胞破坏、骨关节炎、类风湿脊柱炎、痛风性关节炎、炎症性肠病、成人呼吸窘迫综合征（ARDS）、牛皮癣、克罗恩病、过敏性鼻炎、溃疡性结肠炎、过敏反应、接触性皮炎、哮喘、肌肉退化、虚弱、赖特氏综合征、I型糖尿病、II型糖尿病、骨吸收性疾病、移植物抗宿主反应、阿尔茨海默病、中风、心肌梗塞、缺血再灌注损伤、动脉粥样硬化、脑外伤、多发性硬化、脑疟疾、败血症、脓毒性休克、中毒性休克综合征、发热、由HIV-1、HIV-2、HIV-3、巨细胞病毒（CMV）、流感病毒、腺病毒、疱疹病毒或带状疱疹感染引起的肌肉疼痛的方法，包括向哺乳动物施用上述化合物的有效量。
• 4-aryl- and 4-arylthio-5-hydroxy-2(5H)-furanones as inhibitors of
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05464865A1

  公开（公告）日：1995-11-07

  The invention provides novel 5-hydroxy-4-aryl- and 5-hydroxy-4-(arylthio)-2(5H)-furanones of the following structure: ##STR1## wherein R contains from about five to about twenty carbon atoms and is defined herein; X is oxygen, sulfur, SO.sub.2, NH, N(lower alkyl), N(lower acyl), aminocarbonyl, carbonyl, carbonylamino, CH.sub.2 or a carbon-carbon bond; Y is hydrogen, halogen, lower alkyl, nitro, alkylthio, perfluoroalkyl, hydroxy, or lower alkoxy(C.sub.1 -C.sub.8); Z is sulfur or a carbon-carbon bond; and Q is H, an alkyl of from 1-20 carbon atoms, COR', COOR', CONHR', PO(OR')2, PO(OR')R" wherein R' and R" are independently selected from the group consisting of H, an alkyl of from 1-20 carbon atoms, phenyl, and substituted phenyl and prodrugs thereof and pharmaceutically acceptable salts thereof. Pharmaceutical compositions comprising these compounds, methods of using these compounds as inhibitors of inflammation and for treating other diseases characterized by the overproduction of arachidonic acid metabolites, intermediates and methods of preparing these compounds are also provided.

  本发明提供了以下结构的新型5-羟基-4-芳基-和5-羟基-4-(芳硫基)-2(5H)-呋喃酮：其中R含有约五至约二十个碳原子并在此处定义；X是氧、硫、SO.sub.2、NH、N(较低烷基)、N(较低酰基)、氨基甲酰、甲酰、甲酰氨基、CH.sub.2或碳-碳键；Y是氢、卤素、较低烷基、硝基、烷基硫、全氟烷基、羟基或较低烷氧基(C.sub.1 -C.sub.8)；Z是硫或碳-碳键；Q是H、由1-20个碳原子组成的烷基、COR'、COOR'、CONHR'、PO(OR')2、PO(OR')R"，其中R'和R"分别独立选择自H、由1-20个碳原子组成的烷基、苯基和取代苯基及其前药和其药用盐。还提供了包含这些化合物的制药组合物，使用这些化合物作为炎症抑制剂和用于治疗由花生四烯酸代谢产物过度产生所表征的其他疾病的方法，以及制备这些化合物的中间体和方法。
• PPAR-gamma ACTIVATOR
  申请人：KOJUN JAPAN CO., LTD.

  公开号：US20170105965A1

  公开（公告）日：2017-04-20

  The present invention provides A PPARγ activator comprising a butenolide compound represented by the formula (1) or a pharmaceutically acceptable salt thereof: wherein R 1 represents a hydrogen atom, a phosphate group, a fatty acid group, an alkyl group having 1 to 4 carbon atoms and optionally having a substituent or a sugar residue optionally having a substituent, and R 2 represents a phenyl group, a methylphenyl group, a dimethylphenyl group, an ethylphenyl group, a benzyl group, a methylbenzyl group, a dimethylbenzyl group, an ethylbenzyl group, a phenethyl group, a methylphenethyl group, a dimethylphenethyl group, or an ethylphenethyl group.

  本发明提供了一种PPARγ激活剂，包括由式（1）表示的丁烯内酯化合物或其药学上可接受的盐：其中，R1表示氢原子、磷酸盐基团、脂肪酸基团、具有1至4个碳原子的烷基基团，并且可以选择地具有取代基或糖残基，R2表示苯基、甲基苯基、二甲基苯基、乙基苯基、苄基、甲基苄基、二甲基苄基、乙基苄基、苯乙基、甲基苯乙基、二甲基苯乙基或乙基苯乙基。