4-methyl-8-(3-methylbenzoyl)-9-phenylfuro[2,3-h]chromen-2-one

• 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-methyl-8-(3-methylbenzoyl)-9-phenylfuro[2,3-h]chromen-2-one
• 化学式: C₂₆H₁₈O₄
• 分子量: 394.427
• InChiKey: SEJIBHCWBLBNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  8-Benzoyl-7-hydroxy-4-methylcoumarin 、 2-溴-1-间甲苯-乙酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 4-methyl-8-(3-methylbenzoyl)-9-phenylfuro[2,3-h]chromen-2-one
  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

• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING VIRAL INFECTION
  申请人：Hsieh Hsing-Pang

  公开号：US20090312406A1

  公开（公告）日：2009-12-17

  A method for treating an infection with a virus. The method includes administering to a subject in need thereof an effective amount of one or more coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a pharmaceutical composition including a coumarin compound.

  一种治疗病毒感染的方法。该方法包括向需要的受试者施用一种或多种符合以下化学式（I）的香豆素化合物的有效量：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了包括香豆素化合物的药物组合物。
• COUMARIN COMPOUNDS AND THEIR USE FOR TREATING CANCER
  申请人：Hsieh Hsing-Pang

  公开号：US20090312317A1

  公开（公告）日：2009-12-17

  Coumarin compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X are defined herein. Also disclosed is a method for treating cancer with coumarin compounds.

  公式（I）的香豆素化合物：其中R1、R2、R3、R4、R5、R6和X在此定义。还公开了一种使用香豆素化合物治疗癌症的方法。
• US8058427B2
  申请人：——

  公开号：US8058427B2

  公开（公告）日：2011-11-15
• [EN] COUMARIN COMPOUNDS AND THEIR USE FOR TREATING CANCER<br/>[FR] COMPOSÉS DE COUMARINE ET LEUR UTILISATION POUR TRAITER UN CANCER
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2009152210A2

  公开（公告）日：2009-12-17

  Coumarin compounds are disclosed herein. Also disclosed is a method for treating cancer with coumarin compounds.
• 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.