3-hydroxy-6-(hydroxymethyl)-2-(1-hydroxypentyl)-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-6-(hydroxymethyl)-2-(1-hydroxypentyl)-4H-pyran-4-one
• 英文别名: 3-hydroxy-6-hydroxymethyl-2-(1'-hydroxypentyl)-4H-pyran-4-one；3-Hydroxy-6-(hydroxymethyl)-2-(1-hydroxypentyl)pyran-4-one
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: RTSFLYFUVCOFLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  吲哚 、 3-hydroxy-6-(hydroxymethyl)-2-(1-hydroxypentyl)-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2-(1-(1H-indol-3-yl)pentyl)-3-hydroxy-6-(hydroxymethyl)-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 、 正戊醛 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85%的产率得到3-hydroxy-6-(hydroxymethyl)-2-(1-hydroxypentyl)-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

• Microwave-Assisted Condensation of Kojic Acid with Aldehydes
  作者：Pan-Pan Hu、Chun-Feng Zhu、Tao Zhou

  DOI：10.3184/174751912x13383100102119

  日期：2012.8

  Kojic acid derivatives have been prepared in excellent yield by the condensation of two molecules of kojic acid and one molecule of an aldehyde using sodium carbonate as a base under microwave irradiation.

  通过使用碳酸钠作为碱在微波辐射下将两分子曲酸和一分子醛缩合，已经以优异的产率制备曲酸衍生物。
• DRUG FOR AMELIORATING BRAIN DISEASES
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：EP0838220A1

  公开（公告）日：1998-04-29

  The present invention discloses a drug for ameliorating brain diseases which comprises as an active ingredient a compound represented by the following formula (1): [wherein R1 represents H, OH, a lower alkoxyl group, or a lower alkyl group; each of R2 and R3 represents H, a (substituted) lower alkyl group, a lower alkenyl group, a (substituted) phenyl group, or a (substituted) styryl group; and X represents O or a nitrogen atom which may be substituted by a lower alkyl group] or a salt thereof. Because of inhibiting a decrease in brain neurons and promoting branching of neurites, this drug is efficacious in the prevention and treatment of dementia, etc. in association with degeneration and sloughing of brain neurons.

  本发明公开了一种用于改善脑部疾病的药物，其活性成分包括下式（1）所代表的化合物： [其中 R1 代表 H、OH、低级烷氧基或低级烷基；R2 和 R3 各代表 H、（取代的）低级烷基、低级烯基、（取代的）苯基或（取代的）苯乙烯基；X 代表 O 或可被低级烷基取代的氮原子]或其盐。由于这种药物能抑制脑神经元的减少并促进神经元的分枝，因此对预防和治疗与脑神经元退化和脱落有关的痴呆症等具有疗效。
• US5962480A
  申请人：——

  公开号：US5962480A

  公开（公告）日：1999-10-05
• 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.
• Aldol reaction of kojic acid using alumina supported base catalyst and enzymatic resolution of the aldol adduct by CALB
  作者：Deepak K. Sharma、Baldev Singh、Debaraj Mukherjee

  DOI：10.1016/j.tetlet.2014.08.113

  日期：2014.10

  An efficient and ecofriendly aldol reaction of kojic acid with aldehydes using a heterogeneous reusable catalyst (alumina modified with base) is developed. Enzymatic hydrolytic resolution of the racemic acetylated aldol adduct 2 was achieved using lipase from Candida antarctica type B (CALB). The key feature of this enzymatic resolution is that regioselective deacetylation of ester derived from the

  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。