2-(hydroxymethyl)-4-(4-methoxyphenyl)-2H-furan-5-one | 362483-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(hydroxymethyl)-4-(4-methoxyphenyl)-2H-furan-5-one
• CAS: 362483-21-4
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: VRMMBJZNCKTCAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 2-(hydroxymethyl)-4-(4-methoxyphenyl)-2H-furan-5-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-(4-Methoxyphenyl)-5-acetyloxymethyl-2H,5H-furan-2-one
  参考文献：
  名称：

  3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs

  摘要：

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

  DOI：

  10.1021/jm010155x
• 作为产物：
  描述：

  2-(4-methoxyphenyl)pent-4-enoic acid 在 咪唑 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 2-(hydroxymethyl)-4-(4-methoxyphenyl)-2H-furan-5-one
  参考文献：
  名称：

  3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs

  摘要：

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

  DOI：

  10.1021/jm010155x

文献信息

• 3-Phenyl-5-acyloxymethyl-2<i>H</i>,<i>5H</i>-furan-2-ones:  Synthesis and Biological Activity of a Novel Group of Potential Antifungal Drugs
  作者：Milan Pour、Marcel Špulák、Vladimír Buchta、Petra Kubanová、Marie Vopršalová、Vladimír Wsól、Helena Fáková、Petr Koudelka、Hana Pourová、Radan Schiller

  DOI：10.1021/jm010155x

  日期：2001.8.1

  3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34,mug/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 mug/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.