2-ethyl-4-(3-pyridyl)-2H-furan-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-ethyl-4-(3-pyridyl)-2H-furan-5-one
• 英文别名: 2-ethyl-4-pyridin-3-yl-2H-furan-5-one
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: MBUQKKUWZGSUMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-碘吡啶 、 5-ethyl-3-(3-tributylstannyl)-2,5-dihydrofuran-2-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三苯胂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到2-ethyl-4-(3-pyridyl)-2H-furan-5-one
  参考文献：
  名称：

  Cytostatic tetrazole–butenolide conjugates: linking tetrazole and butenolide rings via stille coupling and biological activity of the target substances

  摘要：

  一系列通过苯环连接到丁烯内酯核心的四唑类化合物，是通过α-(三丁基锡基)丁烯内酯和5-(烷基硫基)-1-(4-碘苯基)四唑的斯蒂尔偶联反应制备的，并且对这些化合物进行了抗真菌和细胞毒活性测试。有趣的抗真菌活性针对丝状菌株Absidia corymbifera，以及对白血病细胞HL-60和CCRF-CEM的细胞毒活性被发现。细胞毒活性需要丁烯内酯环和连接到四唑环的烷基硫基团同时存在。此外，还评估了与5-碘四唑进行Pd偶联反应的可行性。

  DOI：

  10.1135/cccc2009040

文献信息

• Synthesis and structure–antifungal activity Relationships of 3-Aryl-5-alkyl-2,5-dihydrofuran-2-ones and Their Carbanalogues: further refinement of tentative pharmacophore group
  作者：Milan Pour、Marcel Špulák、Vojtěch Balšánek、Jiřı́ Kuneš、Petra Kubanová、Vladimı́r Buchta

  DOI：10.1016/s0968-0896(03)00220-7

  日期：2003.7

  Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well. (C) 2003 Elsevier Science Ltd. All rights reserved.