(4-methoxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone | 1207520-82-8

• 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-methoxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone
• 英文别名: (4-methoxy-3-phenylbenzofuran-2-yl)(phenyl)methanone；(4-Methoxy-3-phenyl-1-benzofuran-2-yl)-phenylmethanone
• CAS: 1207520-82-8
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: WWYXUEUWYRBPEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-methoxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(4-hydroxy-3-phenyl-1-benzofuran-2-yl)(phenyl)methanone
  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：

  2-羟基-4-甲氧基苯甲醛 在 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 丙酮 、 均三甲苯 为溶剂， 反应 80.5h， 生成 (4-methoxy-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

文献信息

• An Efficient, Mild and Scalable Synthesis of Bioactive Compounds Containing the Angelicin Scaffold
  作者：Shiao Hui-Yi、Kuo Ching-Chuan、Horng Jim-Tong、Shih Shin-Ru、Chang Sui-Yuan、Liao Chun-Chen、Hsu John T.-A.、Amancha Prashanth Kumar、Chao Yu-Sheng、Hsieh Hsing-Pang

  DOI：10.1002/jccs.201200233

  日期：2012.12

  An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically harsh conditions. The new methodology is applied to the synthesis of several, previously reported analogs of angelicin which have potent anti‐influenza

  开发了一种高效，温和且可扩展的基于安吉林支架的化合物合成方法。特别地，此处描述的新合成路线避免了先前报告的关键Fries重排步骤的需要，该步骤使用了不切实际的苛刻条件。新的方法学被用于合成许多先前报道的具有强力抗流感和抗癌活性的当归霉素类似物。
• Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives
  作者：Jiann-Yih Yeh、Mohane Selvaraj Coumar、Jim-Tong Horng、Hui-Yi Shiao、Fu-Ming Kuo、Hui-Ling Lee、In-Chun Chen、Chun-Wei Chang、Wen-Fang Tang、Sung-Nain Tseng、Chi-Jene Chen、Shin-Ru Shih、John T.-A. Hsu、Chun-Chen Liao、Yu-Sheng Chao、Hsing-Pang Hsieh

  DOI：10.1021/jm901570x

  日期：2010.2.25

  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.
• Palladium-Catalyzed Direct Arylation of Polysubstituted Benzofurans
  作者：Amandine Carrër、Dimitri Brinet、Jean-Claude Florent、Patricia Rousselle、Emmanuel Bertounesque

  DOI：10.1021/jo202060k

  日期：2012.2.3

  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.