2-(3-hydroxy-4-nitrophenyl)quinazolin-4(3H)-one | 36852-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(3-hydroxy-4-nitrophenyl)quinazolin-4(3H)-one
• 英文别名: 2-(3'-Hydroxy-4'-nitrophenyl)-4-chinazolon；2-(3-hydroxy-4-nitro-phenyl)-3H-quinazolin-4-one；2-(3-hydroxy-4-nitro-phenyl)-3H-quinazolin-4-one；2-(3-hydroxy-4-nitrophenyl)-3H-quinazolin-4-one
• CAS: 36852-60-5
• 化学式: C₁₄H₉N₃O₄
• 分子量: 283.243
• InChiKey: VUKBWFNODPQIHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109.12
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-羟基-4-硝基苯甲醛 、 2-氨基苯甲酰胺 在 碘 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以92%的产率得到2-(3-hydroxy-4-nitrophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Scaffold hopping and optimisation of 3’,4’-dihydroxyphenyl- containing thienopyrimidinones: synthesis of quinazolinone derivatives as novel allosteric inhibitors of HIV-1 reverse transcriptase-associated ribonuclease H

  摘要：

  Bioisosteric replacement and scaffold hopping are powerful strategies in drug design useful for rationally modifying a hit compound towards novel lead therapeutic agents. Recently, we reported a series of thienopyrimidinones that compromise dynamics at the p66/p51 HIV-1 reverse transcriptase (RT)-associated Ribonuclease H (RNase H) dimer interface, thereby allosterically interrupting catalysis by altering the active site geometry. Although they exhibited good submicromolar activity, the isosteric replacement of the thiophene ring, a potential toxicophore, is warranted. Thus, in this article, the most active 2-(3,4-dihydroxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 1 was selected as the hit scaffold and several isosteric substitutions of the thiophene ring were performed. A novel series of highly active RNase H allosteric quinazolinone inhibitors was thus obtained. To determine their target selectivity, they were tested against RT-associated RNA-dependent DNA polymerase (RDDP) and integrase (IN). Interestingly, none of the compounds were particularly active on (RDDP) but many displayed micromolar to submicromolar activity against IN.

  DOI：

  10.1080/14756366.2020.1835884