7-hydroxy-4-methyl-8-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]chromen-2-one | 1024743-03-0

• 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: 7-hydroxy-4-methyl-8-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]chromen-2-one
• CAS: 1024743-03-0
• 化学式: C₂₄H₂₆N₂O₃
• 分子量: 390.482
• InChiKey: QRISUDFIMRUHAQ-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-methyl-8-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]chromen-2-one 、 溴丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以46%的产率得到4-methyl-8-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-7-propoxychromen-2-one
  参考文献：
  名称：

  Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae

  摘要：

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.045
• 作为产物：
  描述：

  聚合甲醛 、 羟甲香豆素 、 肉桂基哌嗪 以 乙醇 为溶剂， 以63%的产率得到7-hydroxy-4-methyl-8-[[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]methyl]chromen-2-one
  参考文献：
  名称：

  Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae

  摘要：

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.045

文献信息

• Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae
  作者：Mauro Mazzei、Erika Nieddu、Mariangela Miele、Alessandro Balbi、Marco Ferrone、Maurizio Fermeglia、Marco T. Mazzei、Sabrina Pricl、Paolo La Colla、Fabio Marongiu、Cristina Ibba、Roberta Loddo

  DOI：10.1016/j.bmc.2007.11.045

  日期：2008.3

  Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA(+)). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses. (C) 2007 Elsevier Ltd. All rights reserved.