2-(3,4-Diethoxy-phenyl)-5,7-diethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one | 35800-50-1

• 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: 2-(3,4-Diethoxy-phenyl)-5,7-diethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one
• CAS: 35800-50-1
• 化学式: C₃₅H₄₆O₁₆
• 分子量: 722.741
• InChiKey: NMSINYSYAOTETG-XQZWLAGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  225.43
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-Diethoxy-phenyl)-5,7-diethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one 在 盐酸 、 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 2-[2-(3,4-Diethoxyphenyl)-5,7-diethoxy-4-oxochromen-3-yl]oxyacetic acid
  参考文献：
  名称：

  Pentasubstituted quercetin analogs as selective inhibitors of particulate 3',5'-cyclic-AMP phosphodiesterase from rat brain

  摘要：

  Some penta-O-substituted analogues of quercetin were synthesized and tested for the inhibition of cytosolic and particulate rat brain cyclic AMP and cyclic GMP phosphodiesterase activities. Ten of these compounds are potent and highly selective inhibitors of cAMP hydrolysis with respect to cGMP hydrolysis. They inhibit more potently the particulate enzyme than the cytosolic preparation. The highest selectivity was observed with penta-O-ethylquercetin and analogue 6d, which proved to be more selective and more potent inhibitors than the reference compound Ro 20-1724. Some structure-activity relationships are discussed.

  DOI：

  10.1021/jm00352a019
• 作为产物：
  描述：

  硫酸二乙酯 、 芦丁 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 21.0h， 生成 2-(3,4-Diethoxy-phenyl)-5,7-diethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one
  参考文献：
  名称：

  Pentasubstituted quercetin analogs as selective inhibitors of particulate 3',5'-cyclic-AMP phosphodiesterase from rat brain

  摘要：

  Some penta-O-substituted analogues of quercetin were synthesized and tested for the inhibition of cytosolic and particulate rat brain cyclic AMP and cyclic GMP phosphodiesterase activities. Ten of these compounds are potent and highly selective inhibitors of cAMP hydrolysis with respect to cGMP hydrolysis. They inhibit more potently the particulate enzyme than the cytosolic preparation. The highest selectivity was observed with penta-O-ethylquercetin and analogue 6d, which proved to be more selective and more potent inhibitors than the reference compound Ro 20-1724. Some structure-activity relationships are discussed.

  DOI：

  10.1021/jm00352a019