(4-hydroxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone | 1207520-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (4-hydroxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone
• 英文别名: (4-hydroxy-3-phenylbenzofuran-2-yl)(phenyl)methanone；(4-Hydroxy-3-phenyl-1-benzofuran-2-yl)-phenylmethanone
• CAS: 1207520-84-0
• 化学式: C₂₁H₁₄O₃
• 分子量: 314.34
• InChiKey: MRHWTSNZUPWNSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone 、 巴豆酸酐 在 吡啶 、 咪唑 作用下， 反应 2.0h， 以81%的产率得到(E)-but-2-enoic acid 2-benzoyl-3-phenyl-benzofuran-4-yl ester
  参考文献：
  名称：

  Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives

  摘要：

  By using a cell-based high throughput screening campaign,a novel angelicin derivative 6a was identified to inhibit influenza A (H1N1) virus induced Cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal ill pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h]chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, Which Could form the basis for developing additional defense against influenza pandemics.

  DOI：

  10.1021/jm901570x
• 作为产物：
  描述：

  (4-methoxybenzofuran-2-yl)(phenyl)methanone 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 三甲基乙酸 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 20.0h， 生成 (4-hydroxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Palladium-Catalyzed Direct Arylation of Polysubstituted Benzofurans

  摘要：

  An efficient access to 2-substituted 3-arylbenzofurans through a palladium-catalyzed C3 direct arylation of 2-substituted benzofurans with aryl bromides is described. The scope and limitation of this reaction was studied. The method tolerates a variety of functional groups on the aryl halide and has been successfully extended to polysubstituted benzofurans to obtain the corresponding 3-arylbenzofurans with good to excellent yields.

  DOI：

  10.1021/jo202060k