1-(3-{[tert-butyldimethylsilyl]oxy}-4-methoxyphenyl)-3-(2,3,4-trihydroxyphenyl)-1,3-propanedione | 460744-78-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3-{[tert-butyldimethylsilyl]oxy}-4-methoxyphenyl)-3-(2,3,4-trihydroxyphenyl)-1,3-propanedione
• 英文别名: 1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-3-(2,3,4-trihydroxyphenyl)-1,3-propanedione；1-[3-[Tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]-3-(2,3,4-trihydroxyphenyl)propane-1,3-dione
• CAS: 460744-78-9
• 化学式: C₂₂H₂₈O₇Si
• 分子量: 432.546
• InChiKey: UYCRSXAYMNJYKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-{[tert-butyldimethylsilyl]oxy}-4-methoxyphenyl)-3-(2,3,4-trihydroxyphenyl)-1,3-propanedione 在 硫酸 、 溶剂黄146 作用下， 反应 1.0h， 以42%的产率得到7,8-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Catecholic Flavonoids Acting as Telomerase Inhibitors

  摘要：

  In recent years telomerase has been identified as a new promising target in oncology and consequently new telomerase inhibitors have been intensely explored as anticancer agents. Focused screening of several polyhydroxylated flavonoids has allowed us to identify 7,8,3',4'-tetrahydroxyflavone 1 as a new telomerase inhibitor with an interesting in vitro activity in a Flash-Plate assay (IC50 = 0.2 muM) that has been confirmed in the classical TRAP assay. Starting from this compound, we developed a medicinal chemistry program to optimize our lead, and in particular to replace one of the two catechols with potential bloisosteres. From this study, new structural analogues characterized by submicromolar potencies have been obtained. Their synthesis and biological activity are described.

  DOI：

  10.1021/jm040810b
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸甲酯 在 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(3-{[tert-butyldimethylsilyl]oxy}-4-methoxyphenyl)-3-(2,3,4-trihydroxyphenyl)-1,3-propanedione
  参考文献：
  名称：

  Catecholic Flavonoids Acting as Telomerase Inhibitors

  摘要：

  In recent years telomerase has been identified as a new promising target in oncology and consequently new telomerase inhibitors have been intensely explored as anticancer agents. Focused screening of several polyhydroxylated flavonoids has allowed us to identify 7,8,3',4'-tetrahydroxyflavone 1 as a new telomerase inhibitor with an interesting in vitro activity in a Flash-Plate assay (IC50 = 0.2 muM) that has been confirmed in the classical TRAP assay. Starting from this compound, we developed a medicinal chemistry program to optimize our lead, and in particular to replace one of the two catechols with potential bloisosteres. From this study, new structural analogues characterized by submicromolar potencies have been obtained. Their synthesis and biological activity are described.

  DOI：

  10.1021/jm040810b

文献信息

• Substituted benzopyranones as telomerase inhibitors
  申请人：——

  公开号：US20020160983A1

  公开（公告）日：2002-10-31

  The present invention relates to benzopyranone derivatives, to methods for treating telomerase-modulated diseases, in particular cancers, with said derivatives, to a process for their preparation, to their use as medicaments and to pharmaceutical compositions comprising them.

  本发明涉及苯并吡喃酮衍生物，涉及使用所述衍生物治疗端粒酶调节疾病的方法，特别是癌症，涉及它们的制备过程，它们作为药物的使用，以及包含它们的药物组合物。