5-hydroxy-7,3'-bis(2-ethoxy-2-oxoethoxy)-4'-methoxyflavone | 123580-49-4

• 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-7,3'-bis(2-ethoxy-2-oxoethoxy)-4'-methoxyflavone
• 英文别名: Ethyl 2-[2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-5-hydroxy-4-oxochromen-7-yl]oxyacetate
• CAS: 123580-49-4
• 化学式: C₂₄H₂₄O₁₀
• 分子量: 472.449
• InChiKey: OXBJHKHPSDYCBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  、 5-hydroxy-7,3'-bis(2-ethoxy-2-oxoethoxy)-4'-methoxyflavone 在 potassium carbonate 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-hydroxy-7,3'-bis(2-ethoxy-2-oxoethoxy)-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

• 2-(piperazinyl)-2-oxoethylene-substituted flavonoid compounds
  申请人：Adir et Cie

  公开号：US04970301A1

  公开（公告）日：1990-11-13

  Compound of general formula I: ##STR1## in which: A is a single or double bond, R.sub.1 and R.sub.3, which may be identical or different, are each a hydrogen atom, an alkoxycarbonylmethylene radical of formula --CH.sub.2 CO.sub.2 R.sub.4 (in which R.sub.4 denotes an alkyl radical having 1 to 5 carbon atoms) or a radical of formula W: ##STR2## (in which n is equal to 0 or 1 and R.sub.5, R.sub.6 and R.sub.7, which may be identical or different, are each a hydrogen or halogen atom, a hydroxyl radical, a trifluoromethyl radical, a lower alkyl radical containing 1 to 5 carbon atoms or an alkoxy radical containing 1 to 5 carbon atoms), R.sub.2 is a hydrogen atom, an alkoxycarbonylmethylene radical of formula --CH.sub.2 CO.sub.2 R.sub.4, a radical of formula W, or a .beta.-glucose or rutinose molecule linked to the oxygen to which it is attached with a glycoside bond, on condition, however, that at least either R.sub.1 or R.sub.2 or R.sub.3 always denotes a radical of formula W, and their addition salts with a pharmaceutically acceptable inorganic or organic acid.

  通式I的化合物：##STR1## 其中：A是单键或双键，R.sub.1和R.sub.3可以相同或不同，分别是氢原子，式为--CH.sub.2 CO.sub.2 R.sub.4（其中R.sub.4表示具有1至5个碳原子的烷基基团）的烷氧羰基亚甲基基团或式为W的基团：##STR2##（其中n等于0或1，R.sub.5、R.sub.6和R.sub.7可以相同或不同，分别是氢或卤原子，羟基基团，三氟甲基基团，含有1至5个碳原子的低碳烷基基团或含有1至5个碳原子的烷氧基基团），R.sub.2是氢原子，式为--CH.sub.2 CO.sub.2 R.sub.4的烷氧羰基亚甲基基团，式为W的基团，或与其附着的氧原子以糖苷键连接的β-葡萄糖或芦丁糖分子，但至少R.sub.1或R.sub.2或R.sub.3中的一个始终表示式为W的基团，以及它们与药学上可接受的无机或有机酸的加合盐。
• ROLLAND, YVES;DUHAULT, JACQUES
  作者：ROLLAND, YVES、DUHAULT, JACQUES

  DOI：——

  日期：——
• US4970301A
  申请人：——

  公开号：US4970301A

  公开（公告）日：1990-11-13
• 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.