6-acetyl-2,3-dimethoxyphenyl-4-(acetylamino)-3-nitrobenzoate | 460744-71-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 6-acetyl-2,3-dimethoxyphenyl-4-(acetylamino)-3-nitrobenzoate
• 英文别名: (6-Acetyl-2,3-dimethoxyphenyl) 4-acetamido-3-nitrobenzoate
• CAS: 460744-71-2
• 化学式: C₁₉H₁₈N₂O₈
• 分子量: 402.361
• InChiKey: BKCAPFDIMZOQTN-UHFFFAOYSA-N

物化性质

• 沸点：
  694.8±55.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-acetyl-2,3-dimethoxyphenyl-4-(acetylamino)-3-nitrobenzoate 在 吡啶 、 盐酸 、 氢氧化钾 、 sodium acetate 、 溶剂黄146 、 nickel dichloride 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-(1H-benzimidazol-5-yl)-7,8-dimethoxy-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：

  2'-羟基-3',4'-二甲氧基苯乙酮 、 4-乙酰氨基-3-硝基苯甲酰氯 在 吡啶 作用下， 以78%的产率得到6-acetyl-2,3-dimethoxyphenyl-4-(acetylamino)-3-nitrobenzoate
  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。
• SUBSTITUTED BENZOPYRANONES AS TELOMERASE INHIBITORS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1373244A2

  公开（公告）日：2004-01-02
• [EN] SUBSTITUTED BENZOPYRANONES AS TELOMERASE INHIBITORS<br/>[FR] BENZOPYRANONES SUBSTITUES UTILISES EN TANT QU'INHIBITEURS DE TELOMERASE
  申请人：PHARMACIA ITALIA SPA

  公开号：WO2002074036A2

  公开（公告）日：2002-09-26

  The present invention relates to benzopyranone derivative, 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.