2-(ethylthiomethyl)-5-hydroxy-4H-pyran-4-one | 1257846-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(ethylthiomethyl)-5-hydroxy-4H-pyran-4-one
• 英文别名: 2-(ethylsulfanylmethyl)-5-hydroxypyran-4-one
• CAS: 1257846-09-5
• 化学式: C₈H₁₀O₃S
• 分子量: 186.232
• InChiKey: BOZGBIVLELURMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-氯甲基)-5-羟基-4H-吡喃-4-酮 、 potassium ethanethiolate 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(ethylthiomethyl)-5-hydroxy-4H-pyran-4-one
  参考文献：
  名称：

  Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

  摘要：

  This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.042

文献信息

• Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties
  作者：Ho Sik Rho、Soo Mi Ahn、Dae Sung Yoo、Myung Kyoo Kim、Dong Ha Cho、Jae Youl Cho

  DOI：10.1016/j.bmcl.2010.09.042

  日期：2010.11

  This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities. (C) 2010 Elsevier Ltd. All rights reserved.