Panduratin A; rel-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮 | 89837-52-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: Panduratin A; rel-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮
• 中文别名: PanduratinA;rel-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮；REL-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮
• 英文名称: (+)-Panduratin A
• 英文别名: (2,6-dihydroxy-4-methoxyphenyl)-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
• CAS: 89837-52-5
• 化学式: C₂₆H₃₀O₄
• 分子量: 406.522
• InChiKey: LYDZCXVWCFJAKQ-ZFGGDYGUSA-N

物化性质

• 熔点：
  51 - 76°C
• 沸点：
  563.3±50.0 °C(Predicted)
• 密度：
  1.128
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Panduratin A; rel-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 70.0h， 生成 <5,7-dimethoxy-2-methyl-2-(4'-methylpent-3'-enyl)-2H-chromen-8-yl><3"-methyl-2"-(3"'-methylbut-2"'-enyl-6")-phenylcyclohex-3"-enyl>methanone
  参考文献：
  名称：

  Pancharoen, Orasa; Picker, Kelvin; Reutrakul, Vichai, Australian Journal of Chemistry, 1987, vol. 40, # 3, p. 455 - 459

  摘要：

  DOI：
• 作为产物：
  描述：

  罗勒烯 、 [3-Hydroxy-5-methoxy-2-(3-phenylprop-2-enoyl)phenyl] acetate 在 硼烷四氢呋喃络合物 、 溶剂黄146 、 2R)-(+)-3,3'-二苯基-[2,2'-联二萘]-1,1'-二醇 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 77.0h， 以58%的产率得到Panduratin A; rel-(2,6-二羟基-4-甲氧基苯基)[(1R,2S,6R)-3-甲基-2-(3-甲基-2-丁烯-1-基)-6-苯基-3-环己烯-1-基]甲酮
  参考文献：
  名称：

  手性硼配合物促进的不对称Diels-Alder环加成反应及其在天然产物合成中的应用

  摘要：

  已经成功地开发了一种有效的方法，用于非对称或对称的二烯与二烯基羟基二烯的Diels-Alder环加成反应。Diels–Alder环加成反应是由手性硼与VANOL配合物介导的，可提供高收率的相应产物，并具有出色的非对映和对映选择性。该反应使环己烯骨架的对映选择性结构对于许多Diels-Alder型天然产物（-）-烟酰胺C，（-）-泛地汀A，（-）-kuwanon I，（+）-的全合成至关重要kuwanon J和（-）-溴亚砜A和B.

  DOI：

  10.1021/acs.joc.5b02248

文献信息

• PROPHYLACTIC AGENT AND/OR THERAPEUTIC AGENT FOR CATARACT, MEDICINAL COMPOSITION FOR PREVENTING AND/OR TREATING CATARACT, USE OF PPAR ACTIVATOR FOR PRODUCING SAME, AND EYEDROPS
  申请人：University of Fukui

  公开号：EP3733203A1

  公开（公告）日：2020-11-04

  Provided are agents for prevention and therapeutic treatment of cataract that act by a different mechanism from conventional agents, and use of a PPAR activator for production of such agents. An agent for prevention and/or therapeutic treatment of cataract, containing a PPAR activator as an active ingredient, is used.

  本发明提供了预防和治疗白内障的药剂，其作用机理与传统药剂不同，还提供了使用 PPAR 激活剂生产此类药剂的方法。一种用于预防和/或治疗白内障的药剂含有 PPAR 激活剂作为活性成分。
• Tuntiwachwuttikul, Pittaya; Pancharoen, Orasa; Reutrakul, Vichai, Australian Journal of Chemistry, 1984, vol. 37, # 2, p. 449 - 453
  作者：Tuntiwachwuttikul, Pittaya、Pancharoen, Orasa、Reutrakul, Vichai、Byrne, Lindsay T.

  DOI：——

  日期：——
• An efficient synthesis of (±)-panduratin A and (±)-isopanduratin A, inhibitors of dengue-2 viral activity
  作者：Chin Fei Chee、Iskandar Abdullah、Michael J.C. Buckle、Noorsaadah Abd Rahman

  DOI：10.1016/j.tetlet.2009.11.030

  日期：2010.1

  Panduratin A and its regioisomer isopanduratin A are synthesized in four steps from (E)-ocimene, [(E)-3,7-dimethyl-1,3,6-octatriene] via a Diels-Alder cycloaddition reaction. (C) 2009 Elsevier Ltd. All rights reserved.
• Silver Nanoparticle-Catalyzed Diels−Alder Cycloadditions of 2′-Hydroxychalcones
  作者：Huan Cong、Clinton F. Becker、Sean J. Elliott、Mark W. Grinstaff、John A. Porco

  DOI：10.1021/ja102482b

  日期：2010.6.2

  Metal nanoparticles are currently being employed as catalysts for a number of classical chemical transformations. In contrast, identification of novel reactions of nanoparticles, especially toward the synthesis of complex natural products and derivatives, is highly underdeveloped and represents a bourgeoning area in chemical synthesis. Herein, we report silica-supported silver nanoparticles as solid, recyclable catalysts for Diels-Alder cycloadditions of 2'-hydroxychalcones and dienes in high yield and turnover number. The use of silver nanoparticle catalysts is further demonstrated by the total synthesis of the cytotoxic natural product panduratin A employing a highly electron-rich dienophile and Lewis acid sensitive diene.
• NOVEL USE OF PANDURATIN DERIVATIVE OR BOESENBERGIA PANDURATA EXTRACT
  申请人：Hwang Jae-Kwan

  公开号：US20120088840A1

  公开（公告）日：2012-04-12

  The present invention relates to a novel use of a panduratin derivative or a Boesenbergia pandurata extract. More specifically, the invention relates to a composition for preventing and treating/relieving a metabolic disease selected from a group consisting of obesity, hyperlipidemia, hypercholesterolemia and diabetes, containing a panduratin derivative represented by Chemical Formula 1, 2 or 3 or a Boesenbergia pandurata extract as an active ingredient, a method for treating a metabolic disease selected from a group consisting of obesity, hyperlipidemia, hypercholesterolemia and diabetes, by administering an effective amount of the panduratin derivative or the Boesenbergia pandurata extract to a subject in need thereof, and a use of the panduratin derivative or the Boesenbergia pandurata extract to prepare a reagent for preventing and treating/relieving a metabolic disease selected from a group consisting of obesity, hyperlipidemia, hypercholesterolemia and diabetes. As can be seen foregoing, the present invention provides a novel use of a panduratin derivative or a Boesenbergia pandurata extract. A panduratin derivative or a Boesenbergia pandurata extract of the present invention shows excellent effects on a metabolic disease such as obesity, hyperlipidemia, hypercholesterolemia and diabetes by decreasing highly related causes of metabolic diseases such as on weight, body fat and lipid-content. Since a composition of the present invention is originated from natural materials, it can be used without side effect and provides novel method for preventing and treating/relieving a metabolic disease through body weight loss and body fat loss and the like.