5,3'-dihydroxy-7-(ethoxycarbonylmethoxy)-4'-methoxyflavone | 198886-53-2

• 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: 5,3'-dihydroxy-7-(ethoxycarbonylmethoxy)-4'-methoxyflavone
• 英文别名: Ethyl 2-[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxyacetate
• CAS: 198886-53-2
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: AKBNEOUGZSESFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  、 5,3'-dihydroxy-7-(ethoxycarbonylmethoxy)-4'-methoxyflavone 在 potassium hydrogencarbonate 作用下， 生成
  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
• 作为产物：
  描述：

  香叶木素 、 氯乙酸乙酯 在 potassium hydrogencarbonate 作用下， 生成 5,3'-dihydroxy-7-(ethoxycarbonylmethoxy)-4'-methoxyflavone
  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

• Acides et esters de la diosmetine et les compositions pharmaceutiques les contenant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0803503A1

  公开（公告）日：1997-10-29

  Nouveaux acides et esters de la diosmétine, utilisables comme médicaments et répondant à la formule : dans laquelle R1, R2, R3, R4, R5, R6 et R7 sont tels que définis dans la description, et leurs sels physiologiquement tolérables. Ces dits composés sont utilisables en thérapeutique.

  可用作药物的新的二锇酸及酯类，其式为： 其中 R1、R2、R3、R4、R5、R6 和 R7 如描述中所定义，以及它们在生理上可耐受的盐类。 这些化合物可用于治疗。
• Acides et esters de la diosmétine et compositions pharmaceutiques les contenant
  申请人：ADIR ET COMPAGNIE

  公开号：EP0803503B1

  公开（公告）日：1999-11-03
• US5792789A
  申请人：——

  公开号：US5792789A

  公开（公告）日：1998-08-11
• 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.