3-(3,4-dichlorophenyl)-5-hydroxymethyl-2H,5H-furan-2-one | 362483-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3,4-dichlorophenyl)-5-hydroxymethyl-2H,5H-furan-2-one
• 英文别名: 4-(3,4-dichlorophenyl)-2-(hydroxymethyl)-2H-furan-5-one
• CAS: 362483-59-8
• 化学式: C₁₁H₈Cl₂O₃
• 分子量: 259.089
• InChiKey: HZSJOQGYIUOZOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 3-(3,4-dichlorophenyl)-5-hydroxymethyl-2H,5H-furan-2-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 Acetic acid 4-(3,4-dichloro-phenyl)-5-oxo-2,5-dihydro-furan-2-ylmethyl ester
  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-(3,4-dichlorophenyl)-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 3-(3,4-dichlorophenyl)-5-hydroxymethyl-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

文献信息

• Compounds with antifungal properties and process thereof
  申请人：Gurjar Mukund Keshav

  公开号：US20070259948A1

  公开（公告）日：2007-11-08

  The present invention relates to compounds of formula (1), its solvates and pharmaceutically acceptable salts having antifungal activity and its pharmaceutical composition comprising an effective amount of compound of formula (1) wherein R is substituted alkyl, alkenyl, aryl, heteroaryl, 2-thienyl, 3-thienyl, halothienyl, haloalkyl, halophenyl, or pyrrolyl; and R 1 and R 2 , each independent of the other, are hydrogen, halogen, or alkoxy. The invention also relates to a process for the preparation of said compounds by contacting the intermediate alcohol, prepared from 1,2-O-isopropylideneglyceraldehyde and substituted phenylacetates, with acid chlorides under appropriate conditions to obtain some of the preferred compounds of the invention.

  本发明涉及具有抗真菌活性的化合物的化学式（1），其溶剂合物和药学上可接受的盐，以及包括化学式（1）化合物的有效量的药物组合物，其中R为取代烷基，烯基，芳基，杂芳基，2-噻吩基，3-噻吩基，卤代噻吩基，卤代烷基，卤代苯基或吡咯基；R1和R2，彼此独立，分别为氢，卤素或烷氧基。该发明还涉及一种制备所述化合物的方法，通过将从1,2-O-异丙基亚甲基二羟基丙醛和取代苯乙酸酯制备的中间醇与酸氯化物在适当条件下接触以获得本发明的一些首选化合物。