Methyl 2-(2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)-phenoxy)acetate | 1144104-72-2

• 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: Methyl 2-(2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)-phenoxy)acetate
• 英文别名: Methyl 2-[2-hydroxy-5-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]acetate
• CAS: 1144104-72-2
• 化学式: C₁₈H₁₄O₉
• 分子量: 374.304
• InChiKey: KCOMMXQNUUBGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Methyl 2-(2-(Benzyloxy)-5-(3,7-bis(benzyloxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)phenoxy)acetate 在 氢气 、 palladium(II) hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以75%的产率得到Methyl 2-(2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)-phenoxy)acetate
  参考文献：
  名称：

  Inhibition of Heat Shock Induction of Heat Shock Protein 70 and Enhancement of Heat Shock Protein 27 Phosphorylation by Quercetin Derivatives

  摘要：

  Inhibitors of heat-induced heat shock protein 70 (HSP70) expression have the potential to enhance the therapeutic effectiveness of heat-induced radiosensitization of tumors. Among known small molecule inhibitors, quercetin has the advantage of being easily modified for structure-activity studies. Herein, we report the ability of five monomethyl and five carbomethoxymethyl derivatives of quercetin to inhibit heat-induced HSP70 expression and enhance HSP27 phosphorylation in human cells. While quercetin and several derivatives inhibit HSP70 induction and enhance HSP27 phosphorylation at Ser78, other analogues selectively inhibit HSP70 induction without enhancing HSP27 phosphorylation that would otherwise aid in cell survival. We also show that good inhibitors of HSP70 induction are also good inhibitors of both CK2 and CamKII, kinases that are known to activate HSP70 expression by phosphorylation of heat shock transcription factor 1. Derivatives that show poor inhibition of either or both kinases are not good inhibitors of HSP70 induction, suggesting that quercetin's effectiveness is due to its ability to inhibit both kinases.

  DOI：

  10.1021/jm801445c

文献信息

• QUERCETIN DERIVATIVES AS ANTI-CANCER AGENTS
  申请人：Dabur Pharma Limited

  公开号：EP2185533A2

  公开（公告）日：2010-05-19
• [EN] NOVEL QUERCETIN DERIVATIVES AS ANTI-CANCER AGENTS FIELD OF THE INVENTION<br/>[FR] NOUVEAUX DÉRIVÉS DE QUERCÉTINE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：DABUR PHARMA LTD

  公开号：WO2009019721A2

  公开（公告）日：2009-02-12

  The present invention provides novel Quercetin derivatives of formula (I) and pharmaceutically acceptable salts, hydrates, and solvates thereof, Formula (I): wherein R1 is hydrogen, benzyl or substituted benzyl; R2 is hydrogen, benzyl or substituted benzyl, linear or branched (C1-C6) alkyl, substituted alkyl, aryl, substituted aryl, heterqcyele,and (Substituted heterocycle, useful for treatment of various disorders including cancer, multi-drug resistant cancers, viral infections etc. The invention also provides a process for the preparation of compounds of formula (I) and pharmaceutical compositions comprising the same.