3-hydroxy-2-(hydroxy(phenyl)methyl)-6-(hydroxymethyl)-4H-pyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-hydroxy-2-(hydroxy(phenyl)methyl)-6-(hydroxymethyl)-4H-pyran-4-one
• 英文别名: 3-Hydroxy-6-(hydroxymethyl)-2-[hydroxy(phenyl)methyl]pyran-4-one
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: HLXWZBHLMUUZBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基噻吩 、 3-hydroxy-2-(hydroxy(phenyl)methyl)-6-(hydroxymethyl)-4H-pyran-4-one 在 silica gel supported sulfuric acid 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到3-hydroxy-6-(hydroxymethyl)-2-((5-methylthiophen-2-yl)(phenyl)methyl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of heteroaryl/aryl kojic acid conjugates as stimulators of glucose uptake by GLUT4 translocation

  摘要：

  Insulin exerts its metabolic actions through the insulin receptor (IR) and plays an essential role in treatment of diabetes. The inconvenience of daily injections and the undesirable side-effects associated with insulin injections demand novel drugs for the disease. To search for bioactive insulin mimetic, we synthesized a chemical library of small molecules (2a-3f) based on the indolylkojic acid scaffold (B). An In vitro screening assay was performed to stimulate glucose transport in rat L6 skeletal muscle cells, post treatment of the compounds (2a-3f) for the time period incubation of 16 h. Compounds 2f, 2g, 21, 3a, 3b, 3c and 3d have shown significant glucose uptake stimulation as compared to the controls at micromolar concentrations. In mechanistic studies, we observed that these compounds exert their biological action by enhancing GLUT4 translocation to cell surface via PI3K-dependent signalling pathway in agreement to the insulin mode of action. Hence, these promising conjugates should be useful for further drug development in diabetes treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.041
• 作为产物：
  描述：

  曲酸 、 苯甲醛 在 potassium modified alumina catalysts (CAT₃) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以96%的产率得到3-hydroxy-2-(hydroxy(phenyl)methyl)-6-(hydroxymethyl)-4H-pyran-4-one
  参考文献：
  名称：

  氧化铝负载型碱催化剂对曲酸的醛醇缩醛反应及CALB的酶解反应

  摘要：

  利用多相可重复使用的催化剂（碱改性的氧化铝）开发了曲酸与醛类的高效，环保的醛醇缩醛反应。使用南极假丝酵母B（CALB）的脂肪酶可实现消旋的乙酰化羟醛羟醛加合物2的酶水解。该酶拆分的关键特征是在相邻的仲乙酸盐的存在下，发生自远离立体中心的伯醇衍生的酯的区域选择性脱乙酰化。

  DOI：

  10.1016/j.tetlet.2014.08.113

文献信息

• 一种含愈创兰烃薁结构的曲酸衍生物、制备方法及其应用
  申请人：渤海大学

  公开号：CN109400562B

  公开（公告）日：2022-12-27

  本发明属曲酸类药物化学领域，具体涉及一种含愈创兰烃薁结构的曲酸衍生物、合成及其应用，具有如下结构通式：其中，R为H、烷基、烷氧基、羟基、氨基、卤素、硝基、氰基、羧酸及其酯中的一种。其制备过程是：（1）在醋酸铵的催化下，以水为反应介质，通过愈创兰烃薁与3‑芳基曲酸甲醇进行烷基化反应；（2）反应完毕后，通过直接过滤得到粗产物。（3）重结晶纯化。本发明制备过程原料易得、操作简便、选择性好，通过对曲酸类化合物分子的结构修饰，可以成为获得生物活性化合物的一条重要途径。
• Facile Synthesis of 2-Aryl(guaiazulen-1-yl)methylkojic Acid Derivatives via Benzylation
  作者：Dao-Lin Wang、Xin-Shuang Xiong、Si-Tong Guo、Xiao-Liang Zhang

  DOI：10.3987/com-20-14210

  日期：——

  A facile and efficient one-pot procedure for the preparation of 2-aryl(guaiazulen-l-yl)methylkojic acid derivatives by a catalyst-free, benzylation of guaiazulene with kojic acid-substituted benzylic alcohols under mild conditions in good yield is reported.
• Hydroxypyridinone
  申请人：Novartis AG

  公开号：EP0768302B1

  公开（公告）日：2005-07-06
• US5688815A
  申请人：——

  公开号：US5688815A

  公开（公告）日：1997-11-18
• Synthesis of heteroaryl/aryl kojic acid conjugates as stimulators of glucose uptake by GLUT4 translocation
  作者：Deepak K. Sharma、Jyotsana Pandey、Akhilesh K. Tamrakar、Debaraj Mukherjee

  DOI：10.1016/j.ejmech.2014.08.041

  日期：2014.10

  Insulin exerts its metabolic actions through the insulin receptor (IR) and plays an essential role in treatment of diabetes. The inconvenience of daily injections and the undesirable side-effects associated with insulin injections demand novel drugs for the disease. To search for bioactive insulin mimetic, we synthesized a chemical library of small molecules (2a-3f) based on the indolylkojic acid scaffold (B). An In vitro screening assay was performed to stimulate glucose transport in rat L6 skeletal muscle cells, post treatment of the compounds (2a-3f) for the time period incubation of 16 h. Compounds 2f, 2g, 21, 3a, 3b, 3c and 3d have shown significant glucose uptake stimulation as compared to the controls at micromolar concentrations. In mechanistic studies, we observed that these compounds exert their biological action by enhancing GLUT4 translocation to cell surface via PI3K-dependent signalling pathway in agreement to the insulin mode of action. Hence, these promising conjugates should be useful for further drug development in diabetes treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.