5-Hydroxy-4'-methoxy-7,3'-diacetoxy-flavanon | 3316-45-8

• 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-Hydroxy-4'-methoxy-7,3'-diacetoxy-flavanon
• 英文别名: [2-(3-Acetyloxy-4-methoxyphenyl)-5-hydroxy-4-oxo-2,3-dihydrochromen-7-yl] acetate
• CAS: 3316-45-8
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: HVSFPEVWNQSZNX-UHFFFAOYSA-N

物化性质

• 熔点：
  102.5-103.0 °C
• 沸点：
  579.5±50.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-4'-methoxy-7,3'-diacetoxy-flavanon 在 sodium cyanoborohydride 作用下， 以 三氟乙酸 为溶剂， 以94%的产率得到[4-[3-(3-acetyloxy-4-methoxyphenyl)propyl]-3,5-dihydroxyphenyl] acetate
  参考文献：
  名称：

  氰基硼氢氰化钠三氟乙酰胺中的黄烷酮还原-I /

  摘要：

  在CF 3 COOH中用NaBH 3 CN还原天然黄烷酮，取决于取代基7和4'，产生黄烷或1,3-二芳基丙烷。

  DOI：

  10.1016/s0040-4039(01)93420-3
• 作为产物：
  描述：

  (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 在 吡啶 、 三氟乙酸 作用下， 反应 42.0h， 生成 5-Hydroxy-4'-methoxy-7,3'-diacetoxy-flavanon
  参考文献：
  名称：

  Flavonoid-Related Modulators of Multidrug Resistance:  Synthesis, Pharmacological Activity, and Structure−Activity Relationships

  摘要：

  A series of 28 flavonoid derivatives containing a N-benzylpiperazine chain have been synthesized and tested for their ability to modulate multidrug resistance (MDR) in vitro. At 5 mu M, most compounds potentiated doxorubicin cytotoxicity on resistant K562/DOX cells. They were also able to increase the intracellular accumulation of JC-1, a fluorescent molecule recently described as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. As in other studies, lipophilicity was shown to influence MDR-modulating activity but was not the only determinant. Diverse di- and trimethoxy substitutions on N-benzyl were examined and found to affect the activity differently. The most active compounds had a 2,3,4-trimethoxybenzylpiperazine chain attached to either a flavone or a flavanone moiety (13, 19, 33, and 37) and were found to be more potent; than verapamil.

  DOI：

  10.1021/jm981064b

文献信息

• LEWIN, GUY;BERT, MARYSE;DAUGUET, JEAN-CLAUDE;SCHAEFFER, CORINNE;GUINAMANT+, TETRAHEDRON LETT., 30,(1989) N0, C. 7049-7052
  作者：LEWIN, GUY、BERT, MARYSE、DAUGUET, JEAN-CLAUDE、SCHAEFFER, CORINNE、GUINAMANT+

  DOI：——

  日期：——
• Flavonoid-Related Modulators of Multidrug Resistance:  Synthesis, Pharmacological Activity, and Structure−Activity Relationships
  作者：Jacques Ferté、Jean-Marc Kühnel、Geneviève Chapuis、Yves Rolland、Guy Lewin、Marc A. Schwaller

  DOI：10.1021/jm981064b

  日期：1999.2.1

  A series of 28 flavonoid derivatives containing a N-benzylpiperazine chain have been synthesized and tested for their ability to modulate multidrug resistance (MDR) in vitro. At 5 mu M, most compounds potentiated doxorubicin cytotoxicity on resistant K562/DOX cells. They were also able to increase the intracellular accumulation of JC-1, a fluorescent molecule recently described as a probe of P-glycoprotein-mediated MDR. This suggests that these compounds act, at least in part, by inhibiting P-glycoprotein activity. As in other studies, lipophilicity was shown to influence MDR-modulating activity but was not the only determinant. Diverse di- and trimethoxy substitutions on N-benzyl were examined and found to affect the activity differently. The most active compounds had a 2,3,4-trimethoxybenzylpiperazine chain attached to either a flavone or a flavanone moiety (13, 19, 33, and 37) and were found to be more potent; than verapamil.
• Reduction de flavanones par le cyanoborohydrure de sodium dans l'acide trifluoroacetique - I/
  作者：Guy Lewin、Maryse Bert、Jean-Claude Dauguet、Corinne Schaeffer、Jean-Luc Guinamant、Jean-Paul Volland

  DOI：10.1016/s0040-4039(01)93420-3

  日期：——

  Reduction of natural flavanones with NaBH3CN in CF3COOH gives, depending on substituents 7 and 4′, either flavanes or 1,3-diaryl propanes.

  在CF 3 COOH中用NaBH 3 CN还原天然黄烷酮，取决于取代基7和4'，产生黄烷或1,3-二芳基丙烷。