4'-(benzyloxy)-5,7-dihydroxy-3-methoxyflavone | 1486-59-5

• 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: 4'-(benzyloxy)-5,7-dihydroxy-3-methoxyflavone
• 英文别名: 2-(4-Benzyloxy-phenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-on；3-Methyl-4'-benzyl-kaempferol；4'-Benzyl-3-methyl-kaempferol；3-Methyl-4'-benzyl-kampferol；2-(4-benzyloxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-one；2-(4-Benzyloxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on；5,7-Dihydroxy-3-methoxy-2-(4-phenylmethoxyphenyl)chromen-4-one
• CAS: 1486-59-5
• 化学式: C₂₃H₁₈O₆
• 分子量: 390.392
• InChiKey: XUARALITUYJQAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-(benzyloxy)-5,7-dihydroxy-3-methoxyflavone 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 kaempferol-3,5,7-trimethyl ether
  参考文献：
  名称：

  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

  摘要：

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

  DOI：

  10.1021/jm00106a039
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-甲氧基-1-乙酮 、 4-苄氧基苯甲酸酐 生成 4'-(benzyloxy)-5,7-dihydroxy-3-methoxyflavone
  参考文献：
  名称：

  DE, MEYER NADINE;HAEMERS, ACHIEL;MISHRA, LALLAN;PANDEY, HRISHI-KESH;PIETE+, J. MED. CHEM., 34,(1991) N, C. 736-746

  摘要：

  DOI：

文献信息

• Kobayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1
  作者：Kobayashi

  DOI：——

  日期：——
• PANDEY, H. K.;DE, MEYER N.;MISHRA, L.;HAEMERS, A.;PIETERS, L. A.;BERGHE, +, J. PHARM. BELG., 43,(1988) N, C. 303-305
  作者：PANDEY, H. K.、DE, MEYER N.、MISHRA, L.、HAEMERS, A.、PIETERS, L. A.、BERGHE, +

  DOI：——

  日期：——
• DE, MEYER NADINE;HAEMERS, ACHIEL;MISHRA, LALLAN;PANDEY, HRISHI-KESH;PIETE+, J. MED. CHEM., 34,(1991) N, C. 736-746
  作者：DE, MEYER NADINE、HAEMERS, ACHIEL、MISHRA, LALLAN、PANDEY, HRISHI-KESH、PIETE+

  DOI：——

  日期：——
• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.