6,7-difluoro-2-methyl-3-phenylquinazolin-4(3H)-one | 1314492-92-6

• 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: 6,7-difluoro-2-methyl-3-phenylquinazolin-4(3H)-one
• 英文别名: 2-methyl-3-phenyl-6,7-difluoro-3H-quinazolin-4-one
• CAS: 1314492-92-6
• 化学式: C₁₅H₁₀F₂N₂O
• 分子量: 272.254
• InChiKey: XLAHOXHZOFSGGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6,7-difluoro-2-methyl-3-phenylquinazolin-4(3H)-one 在 sodium acetate 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-4-(2-(6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)vinyl)-N-(3-(pyrrolidin-1-yl)propyl)benzamide
  参考文献：
  名称：

  Synthesis and Evaluation of Quinazolone Derivatives as a New Class of c-KIT G-Quadruplex Binding Ligands

  摘要：

  The c-KIT G-quadruplex structures are a novel class of attractive targets for the treatment of gastrointestinal stromal tumor (GIST). Herein, a series of new quinazolone derivatives with the expansion of unfused aromatic ring system were designed and synthesized. Subsequent biophysical studies demonstrated that the derivatives with adaptive scaffold could effectively bind to and stabilize c-KIT G-quadruplexes with good selectivity against duplex DNA. More importantly, these ligands further inhibited the transcription and expression of c-KIT gene and exhibited significant cytotoxicity on the GIST cell line HGC-27. Overall, these quinazolone derivatives represent a new class of promising c-KIT G-quadruplex ligands. The experimental results have also reinforced the idea of inhibition of c-KIT expression through targeting c-KIT G-quadruplex DNA.

  DOI：

  10.1021/ml400271y
• 作为产物：
  描述：

  2-氨基-4,5-二氟苯甲酸 反应 14.0h， 生成 6,7-difluoro-2-methyl-3-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and Evaluation of Quinazolone Derivatives as a New Class of c-KIT G-Quadruplex Binding Ligands

  摘要：

  The c-KIT G-quadruplex structures are a novel class of attractive targets for the treatment of gastrointestinal stromal tumor (GIST). Herein, a series of new quinazolone derivatives with the expansion of unfused aromatic ring system were designed and synthesized. Subsequent biophysical studies demonstrated that the derivatives with adaptive scaffold could effectively bind to and stabilize c-KIT G-quadruplexes with good selectivity against duplex DNA. More importantly, these ligands further inhibited the transcription and expression of c-KIT gene and exhibited significant cytotoxicity on the GIST cell line HGC-27. Overall, these quinazolone derivatives represent a new class of promising c-KIT G-quadruplex ligands. The experimental results have also reinforced the idea of inhibition of c-KIT expression through targeting c-KIT G-quadruplex DNA.

  DOI：

  10.1021/ml400271y

文献信息

• Synthesis and photophysical properties of 2-styrylquinazolin-4-ones
  作者：T. V. Trashakhova、E. V. Nosova、M. S. Valova、P. A. Slepukhin、G. N. Lipunova、V. N. Charushin

  DOI：10.1134/s1070428011050150

  日期：2011.5

  trans-2-Styryl-substituted 3H-, 3-phenyl-, and 3-naphthylquinazolin-4-ones and their 6,7-difluoro derivatives were synthesized by condensation of appropriate 2-methylquinazolin-4-ones with aromatic aldehydes or by the transformation of the heterocycle of 2-methyl-3,1-benzoxazin-4-one under the action of benzylidenephenylamines.