2-((4-fluorophenylthio)methyl)-5-hydroxy-4H-pyran-4-one | 500861-19-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((4-fluorophenylthio)methyl)-5-hydroxy-4H-pyran-4-one
• 英文别名: 5-hydroxy-2-((4-fluorophenylthio)methyl)-4H-pyran-4-one；2-(((4-fluorophenyl)thio)methyl)-5-hydroxy-4H-pyran-4-one；2-[(4-fluorophenyl)sulfanylmethyl]-5-hydroxypyran-4-one
• CAS: 500861-19-8
• 化学式: C₁₂H₉FO₃S
• 分子量: 252.266
• InChiKey: AJMZFXUDUORRMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((4-fluorophenylthio)methyl)-5-hydroxy-4H-pyran-4-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-hydroxy-2-((4-fluorophenylsulfinyl)methyl)-4H-pyran-4-one
  参考文献：
  名称：

  Inhibitory Activities of Kojyl Thioether Derivatives against Nitric Oxide Production Induced by Lipopolysaccharide

  摘要：

  DOI：

  10.5012/bkcs.2010.31.11.3463
• 作为产物：
  描述：

  2-((4-fluorophenylthio)methyl)-5-(4-methoxybenzyloxy)-4H-pyran-4-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以61%的产率得到2-((4-fluorophenylthio)methyl)-5-hydroxy-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase

  摘要：

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.062

文献信息

• Asymmetric Michael addition between kojic acid derivatives and unsaturated ketoesters promoted by <i>C</i>₂-symmetric organocatalysts
  作者：Alexey A. Kostenko、Alexander S. Kucherenko、Andrey N. Komogortsev、Boris V. Lichitsky、Sergei G. Zlotin

  DOI：10.1039/c8ob02523a

  日期：——

  An efficient sterically hindered C2-symmetric bifunctional tertiary amine–squaramide organocatalyst for the asymmetric Michael addition/hemiketalization domino reaction of kojic acid derivatives with β,γ-unsaturated α-ketoesters has been designed. Pharmacology-relevant functionalized 2,3,4,8-tetrahydropyrano[3,2-b]pyran derivatives were produced over the catalyst in as low as 1 mol% with up to 99%

  设计了一种高效的位阻C 2对称双官能叔胺-方酰胺有机催化剂，用于曲酸衍生物与β，γ-不饱和α-酮酸酯的不对称迈克尔加成/半缩酮化多米诺反应。在催化剂上以低至1 mol％的产率制备了药理学相关的官能化2,3,4,8-四氢吡喃并[3,2- b ]吡喃衍生物，产率高达99％，ee高达99％。该程序至少可扩展30倍，并且该催化剂可通过酸碱萃取容易地用于催化反应中。用（S）-或rac酰化产物-布洛芬和十一碳烯酸与相应的手性酯含有两个特权药效基序。
• Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates
  作者：Ruslan A. Kovalevsky、Maxim V. Smirnov、Alexander S. Kucherenko、Kseniya A. Bykova、Elizaveta V. Shikina、Sergei G. Zlotin

  DOI：10.1002/ejoc.202101435

  日期：2022.1.21

  Chiral nitro compounds containing two hydroxypyranone units were enantioselectively produced from kojic acid derivatives and 2-nitroallylic carbonates in the presence of bifunctional tertiary amine-squaramide organocatalyst. The reaction products were converted to corresponding acetates and nitro glutarates via acylation or oxidative fragmentation reactions.

  在双功能叔胺-方酰胺有机催化剂存在下，由曲酸衍生物和 2-硝基烯丙基碳酸酯对映选择性地制备了含有两个羟基吡喃酮单元的手性硝基化合物。反应产物通过酰化或氧化断裂反应转化为相应的乙酸盐和硝基戊二酸盐。
• Discovery of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221) as a functional antagonist of the apelin (APJ) receptor
  作者：Patrick R. Maloney、Pasha Khan、Michael Hedrick、Palak Gosalia、Monika Milewski、Linda Li、Gregory P. Roth、Eduard Sergienko、Eigo Suyama、Eliot Sugarman、Kevin Nguyen、Alka Mehta、Stefan Vasile、Ying Su、Derek Stonich、Hung Nguyen、Fu-Yue Zeng、Arianna Mangravita Novo、Michael Vicchiarelli、Jena Diwan、Thomas D.Y. Chung、Layton H. Smith、Anthony B. Pinkerton

  DOI：10.1016/j.bmcl.2012.08.105

  日期：2012.11

  The recently discovered apelin/APJ system has emerged as a critical mediator of cardiovascular homeostasis and is associated with the pathogenesis of cardiovascular disease. A role for apelin/APJ in energy metabolism and gastrointestinal function has also recently emerged. We disclose the discovery and characterization of 4-oxo-6-((pyrimidin-2-ylthio)methyl)-4H-pyran-3-yl 4-nitrobenzoate (ML221), a potent APJ functional antagonist in cell-based assays that is >37-fold selective over the closely related angiotensin II type 1 (AT1) receptor. ML221 was derived from an HTS of the similar to 330,600 compound MLSMR collection. This antagonist showed no significant binding activity against 29 other GPCRs, except to the kappa-opioid and benzodiazepinone receptors (<50/<70%I at 10 mu M). The synthetic methodology, development of structure-activity relationship (SAR), and initial in vitro pharmacologic characterization are also presented. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase
  作者：Mithun Raje、Niyada Hin、Bridget Duvall、Dana V. Ferraris、James F. Berry、Ajit G. Thomas、Jesse Alt、Camilo Rojas、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2013.04.062

  日期：2013.7

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.
• Inhibitory Activities of Kojyl Thioether Derivatives against Nitric Oxide Production Induced by Lipopolysaccharide
  作者：Ho-Sik Rho、Dae-Sung Yoo、Soo-Mi Ahn、Myung-Kyoo Kim、Dong-Ha Cho、Jae-Youl Cho

  DOI：10.5012/bkcs.2010.31.11.3463

  日期：2010.11.20