6-methyl-5'-benzyl-2'-hydroxyflavone | 1093116-22-3

• 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: 6-methyl-5'-benzyl-2'-hydroxyflavone
• 英文别名: 2-(5-benzyl-2-hydroxyphenyl)-6-methyl-4H-chromen-4-one；2-(5-benzyl-2-hydroxyphenyl)-6-methylchromen-4-one
• CAS: 1093116-22-3
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: UHHVZGAPCPFAGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl-9-borabicyclo[3.3.1]nonane 、 6-methyl-5'-bromo-2'-hydroxyflavone 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以57%的产率得到6-methyl-5'-benzyl-2'-hydroxyflavone
  参考文献：
  名称：

  Azaflavones compared to flavones as ligands to the benzodiazepine binding site of brain GABAA receptors

  摘要：

  A series of azaflavone derivatives and analogues were prepared and evaluated for their affinity to the benzodiazepine binding site of the GABA(A) receptor, and compared to their flavone counterparts. Three of the compounds, the azaflavones 9 and 12 as well as the new flavone 13, were also assayed on GABAA receptor subtypes (alpha(1)beta(3)gamma(2s), alpha(2)beta(3)gamma(2s), alpha(4)beta(3)gamma(2s) and alpha(5)beta(3)gamma(2s)), displaying nanomolar affinities as well as selectivity for alpha 1- versus alpha 2- and alpha 3-containing receptors by a factor of between 14 and 26. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.092

文献信息

• Azaflavones compared to flavones as ligands to the benzodiazepine binding site of brain GABAA receptors
  作者：Jakob Nilsson、Elsebet Østergaard Nielsen、Tommy Liljefors、Mogens Nielsen、Olov Sterner

  DOI：10.1016/j.bmcl.2008.09.092

  日期：2008.11

  A series of azaflavone derivatives and analogues were prepared and evaluated for their affinity to the benzodiazepine binding site of the GABA(A) receptor, and compared to their flavone counterparts. Three of the compounds, the azaflavones 9 and 12 as well as the new flavone 13, were also assayed on GABAA receptor subtypes (alpha(1)beta(3)gamma(2s), alpha(2)beta(3)gamma(2s), alpha(4)beta(3)gamma(2s) and alpha(5)beta(3)gamma(2s)), displaying nanomolar affinities as well as selectivity for alpha 1- versus alpha 2- and alpha 3-containing receptors by a factor of between 14 and 26. (C) 2008 Elsevier Ltd. All rights reserved.