5-acetoxy-2-methyl-pyran-4-one | 54917-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-acetoxy-2-methyl-pyran-4-one
• 英文别名: 6-methyl-4-oxo-4H-pyran-3-yl acetate；Acetylallomaltol；(6-methyl-4-oxopyran-3-yl) acetate
• CAS: 54917-86-1
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: PMCYKVQJIDOBRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-acetoxy-2-methyl-pyran-4-one 在 水 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 作用下， 生成 1-biphenyl-3-yl-5-hydroxy-2-methylpyridin-4(1H)-one
  参考文献：
  名称：

  Synthesis and Evaluation of Heterocyclic Catechol Mimics as Inhibitors of Catechol-O-methyltransferase (COMT)

  摘要：

  3-Hydroxy-4-pyridinones and 5-hydroxy-4-pyrimidinones were identified as inhibitors of catechol-O-methyltransferase (COMT) in a high throughput screen. These heterocyclic catechol mimics exhibit potent inhibition of the enzyme and an improved toxicity profile versus the marketed nitrocatechol inhibitors tolcapone and entacapone. Optimization of the series was aided by X-ray cocrystal structures of the novel inhibitors in complex with COMT and cofactors SAM and Mg2+. The crystal structures suggest a mechanism of inhibition for these heterocyclic inhibitors distinct from previously disclosed COMT inhibitors.

  DOI：

  10.1021/ml500502d
• 作为产物：
  描述：

  在 4-甲基苯磺酸吡啶 作用下， 生成 5-acetoxy-2-methyl-pyran-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Heterocyclic Catechol Mimics as Inhibitors of Catechol-O-methyltransferase (COMT)

  摘要：

  3-Hydroxy-4-pyridinones and 5-hydroxy-4-pyrimidinones were identified as inhibitors of catechol-O-methyltransferase (COMT) in a high throughput screen. These heterocyclic catechol mimics exhibit potent inhibition of the enzyme and an improved toxicity profile versus the marketed nitrocatechol inhibitors tolcapone and entacapone. Optimization of the series was aided by X-ray cocrystal structures of the novel inhibitors in complex with COMT and cofactors SAM and Mg2+. The crystal structures suggest a mechanism of inhibition for these heterocyclic inhibitors distinct from previously disclosed COMT inhibitors.

  DOI：

  10.1021/ml500502d

文献信息

• 5-HYDROXY-2-METHYL-4H-PYRAN-4-ONE ESTERS AS NOVEL TYROSINASE INHIBITORS
  申请人：Wempe Michael Fitzpatrick

  公开号：US20090215887A1

  公开（公告）日：2009-08-27

  Skin brightening compositions based on esters of 5-hydroxy-2-methyl-4H-pyran-4-one. Also disclosed are methods of making the compositions as well as methods of using the compositions.

  基于5-羟基-2-甲基-4H-吡喃-4-酮酯的美白肌肤配方。还公开了制备这些配方的方法以及使用这些配方的方法。
• 5-Hydroxy-2-Methyl-4H-Pyran-4-One Esters as Novel Tyrosinase Inhibitors
  申请人：Wempe Michael Fitzpatrick

  公开号：US20100216873A1

  公开（公告）日：2010-08-26

  Skin brightening compositions based on esters of 5-hydroxy-2-methyl-4H-pyran-4-one. Also disclosed are methods of making the compositions as well as methods of using the compositions.

  基于5-羟基-2-甲基-4H-吡喃-4-酮酯的皮肤美白组合物。还公开了制备该组合物的方法以及使用该组合物的方法。
• 5-hydroxy-2-methyl-4H-pyran-4-one esters as novel tyrosinase inhibitors
  申请人：Eastman Chemical Company

  公开号：US08183398B2

  公开（公告）日：2012-05-22

  Skin brightening compositions based on esters of 5-hydroxy-2-methyl-4H-pyran-4-one. Also disclosed are methods of making the compositions as well as methods of using the compositions.

  基于5-羟基-2-甲基-4H-吡喃-4-酮酯的美白配方。本发明还公开了制备该配方的方法以及使用该配方的方法。
• 5-HYDROXY-2-METHYL-4H-PYRAN-4-ONE-ESTERS AS NOVEL TYROSINASE INHIBITORS
  申请人：Eastman Chemical Company

  公开号：EP2245024A1

  公开（公告）日：2010-11-03
• US8183398B2
  申请人：——

  公开号：US8183398B2

  公开（公告）日：2012-05-22