4-methyl-7-m-toluoyloxy-coumarin | 304673-29-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methyl-7-m-toluoyloxy-coumarin
• 英文别名: 4-Methyl-7-m-toluoyloxy-cumarin；4-methyl-2-oxo-2H-chromen-7-yl 3-methylbenzoate；(4-methyl-2-oxochromen-7-yl) 3-methylbenzoate
• CAS: 304673-29-8
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: JFEPYPGHXXDEMT-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C(Solv: ethanol (64-17-5))
• 沸点：
  482.2±45.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-7-m-toluoyloxy-coumarin 在 三氯化铝 作用下， 生成 7-benzoyloxy-4-methyl-8-m-toluoyl-coumarin
  参考文献：
  名称：

  Bhagwat; Shahane, Rasayanam, 1939, vol. 1, p. 191,194

  摘要：

  DOI：
• 作为产物：
  描述：

  羟甲香豆素 、 间甲基苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-methyl-7-m-toluoyloxy-coumarin
  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

文献信息

• 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.
• Bhagwat; Shahane, Rasayanam, 1939, vol. 1, p. 191,194
  作者：Bhagwat、Shahane

  DOI：——

  日期：——