3-(4-Bromophenyl)-5-(hydroxymethyl)oxolan-2-one | 362483-77-0

• 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-(4-Bromophenyl)-5-(hydroxymethyl)oxolan-2-one
• CAS: 362483-77-0
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: OFBSXWWPNPFXLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-(4-Bromophenyl)-5-(hydroxymethyl)oxolan-2-one 在 吡啶 、 咪唑 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.5h， 生成 3-(4-bromophenyl)-5-acetyloxymethyl-2,5-dihydrofuran-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：

  4-溴苯乙酸甲酯 在 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 24.5h， 生成 3-(4-Bromophenyl)-5-(hydroxymethyl)oxolan-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

• Antifungal 3,5-disubstituted furanones: From 5-acyloxymethyl to 5-alkylidene derivatives
  作者：Petr Šenel、Lucie Tichotová、Ivan Votruba、Vladimír Buchta、Marcel Špulák、Jiří Kuneš、Milan Nobilis、Ondřej Krenk、Milan Pour

  DOI：10.1016/j.bmc.2010.01.030

  日期：2010.3

  parent furanone structure were therefore prepared and evaluated. In line with the ease of elimination of the substituent from C5, low activities of the 5-alkoxy compounds were observed. On the other hand, their 5-aryloxymethyl congeners were found to be capable of liberating the antifungally active 5-methylene furanone into the testing medium. The antifungal effect of the 5-alkylidene derivatives was

  发现先前描述为高度抗真菌活性的5-乙酰氧基甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮可通过DMSO异常消除C5处的酯基来提供相应的5-亚甲基衍生物在抗真菌试验条件下。由于后者具有与最初报道的抗真菌作用几乎相同的抗真菌作用，因此5-乙酰氧基甲基呋喃酮仅用作实际的抗真菌活性物质的前体。因此，制备并评估了一系列在母体呋喃酮结构的C5处具有烷氧基，芳氧基和亚烷基取代基的化合物。与从C5中消除取代基的容易性相一致，观察到5-烷氧基化合物的活性低。另一方面，发现它们的5-芳氧基甲基同源物能够将抗真菌活性的5-亚甲基呋喃酮释放到测试介质中。5-亚烷基衍生物的抗真菌作用对亚烷基部分的取代高度敏感。为了保持化合物的高活性，在烯丙基位置的取代基是必需的。细胞抑制活性的并行评估显示抗真菌活性衍生物对HeLa S3和CCRF-CEM系的中等活性。用5-亚甲基-3-（4-溴苯基）-2,5-二氢呋喃-2-酮处
• 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.