5,7-dihydroxy-3-(3-nitrobenzyloxy)-2-phenyl-4H-chromen-4-one | 1236113-95-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5,7-dihydroxy-3-(3-nitrobenzyloxy)-2-phenyl-4H-chromen-4-one
• 英文别名: 5,7-Dihydroxy-3-[(3-nitrophenyl)methoxy]-2-phenyl-chromen-4-one；5,7-dihydroxy-3-[(3-nitrophenyl)methoxy]-2-phenylchromen-4-one
• CAS: 1236113-95-3
• 化学式: C₂₂H₁₅NO₇
• 分子量: 405.364
• InChiKey: XJFLBWVLJXRNSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 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：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(tert-butyldimethylsilyloxy)-5,7-dihydroxy-2-phenyl-4H-chromen-4-one 、 3-硝基溴苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 5,7-dihydroxy-3-(3-nitrobenzyloxy)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  3-O-Arylmethylgalangin, a novel isostere for anti-HCV 1,3-diketoacids (DKAs)

  摘要：

  Through chelation of the metal ions at the enzyme active site, 1,3-diketoacids (DKAs) show potent inhibition of viral enzymes such as HIV integrase and HCV NS5B. In order to optimize the antiviral activity of the DKAs, structural modification of their metal-binding units, keto-enol acids or monoketo acids, have been actively performed. In this study, we proposed 3-O-arylmethylgalangin 3 as an alternative to ortho-substituted aromatic DKA, a potent inhibitor of HCV NS5B. As a proof-of-concept study, a series of 3-O-arylmethylgalangin derivatives (3a-3r) were prepared and their inhibitory activity against HCV NS5B was estimated. Structure-activity relationship of the 3-O-arylmethylgalangin derivatives was in good accordance with that of the ortho-substituted aromatic DKA series. In particular, two galangin ethers (3g and 3i) completely superimposable with the most potent ortho-substituted aromatic DKA analogue (2) in atom-by-atom fashion showed equipotent inhibitory activity to that of 2. Taken together, this result provides convincing evidence that the 3-O-arylmethylgalangin can successfully mimic the chelating function of the DKA pharmacophore to show potent inhibitory activity against the target enzyme, HCV NS5B. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.021

文献信息

• 3-O-Arylmethylgalangin, a novel isostere for anti-HCV 1,3-diketoacids (DKAs)
  作者：Hyo Seon Lee、Kwang-su Park、Bokhui Lee、Dong-Eun Kim、Youhoon Chong

  DOI：10.1016/j.bmc.2010.09.021

  日期：2010.11

  Through chelation of the metal ions at the enzyme active site, 1,3-diketoacids (DKAs) show potent inhibition of viral enzymes such as HIV integrase and HCV NS5B. In order to optimize the antiviral activity of the DKAs, structural modification of their metal-binding units, keto-enol acids or monoketo acids, have been actively performed. In this study, we proposed 3-O-arylmethylgalangin 3 as an alternative to ortho-substituted aromatic DKA, a potent inhibitor of HCV NS5B. As a proof-of-concept study, a series of 3-O-arylmethylgalangin derivatives (3a-3r) were prepared and their inhibitory activity against HCV NS5B was estimated. Structure-activity relationship of the 3-O-arylmethylgalangin derivatives was in good accordance with that of the ortho-substituted aromatic DKA series. In particular, two galangin ethers (3g and 3i) completely superimposable with the most potent ortho-substituted aromatic DKA analogue (2) in atom-by-atom fashion showed equipotent inhibitory activity to that of 2. Taken together, this result provides convincing evidence that the 3-O-arylmethylgalangin can successfully mimic the chelating function of the DKA pharmacophore to show potent inhibitory activity against the target enzyme, HCV NS5B. (C) 2010 Elsevier Ltd. All rights reserved.