5,7-dihydroxy-3'-(ethoxycarbonylmethoxy)-4'-methoxyflavone | 123580-44-9

• 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: 5,7-dihydroxy-3'-(ethoxycarbonylmethoxy)-4'-methoxyflavone
• 英文别名: 3'-O-(ethoxycarbonylmethyl)diosmetin；Ethyl 2-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenoxy]acetate
• CAS: 123580-44-9
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: IRNXXXUUGDIFRS-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：

  5,7-dihydroxy-3'-(ethoxycarbonylmethoxy)-4'-methoxyflavone 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~120.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成 Ethyl 2-[5-[5-hydroxy-7-[2-[4-[(4-hydroxy-2,3-dimethoxyphenyl)methyl]piperazin-1-yl]-2-oxoethoxy]-4-oxochromen-2-yl]-2-methoxyphenoxy]acetate
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of a series of piperazinyl flavones

  摘要：

  A series of 27 flavonoid derivatives containing a piperazinyl chain have been synthesized and tested for their antiplasmodial activity. Diverse substitution patterns on piperazinyl and flavone moieties were examined and found to affect the activity differently. The most active compounds, which have a 2,3,4-trimethoxybenzylpiperazinyl chain attached to the flavone at the 7-phenol group, showed in vitro activity against chloroquine-sensitive (Thai) and -resistant (FcB1,K1) Plasmodium falciparum strains in the micromolar to submicromolar range. One of them was active when given orally in a Plasmodium yoelii nigeriensis infected mouse model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.051
• 作为产物：
  描述：

  diosmin 在 盐酸 、 potassium hydrogencarbonate 、 对甲苯磺酸 作用下， 反应 8.05h， 生成 5,7-dihydroxy-3'-(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

• 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
• Synthesis and antimalarial evaluation of a series of piperazinyl flavones
  作者：Gwenola Auffret、Mehdi Labaied、François Frappier、Philippe Rasoanaivo、Philippe Grellier、Guy Lewin

  DOI：10.1016/j.bmcl.2006.11.051

  日期：2007.2

  A series of 27 flavonoid derivatives containing a piperazinyl chain have been synthesized and tested for their antiplasmodial activity. Diverse substitution patterns on piperazinyl and flavone moieties were examined and found to affect the activity differently. The most active compounds, which have a 2,3,4-trimethoxybenzylpiperazinyl chain attached to the flavone at the 7-phenol group, showed in vitro activity against chloroquine-sensitive (Thai) and -resistant (FcB1,K1) Plasmodium falciparum strains in the micromolar to submicromolar range. One of them was active when given orally in a Plasmodium yoelii nigeriensis infected mouse model. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.