4-(3-fluoro-4-methylanilino)-6,7-dimethoxyquinazoline | 1268310-02-6

• 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: 4-(3-fluoro-4-methylanilino)-6,7-dimethoxyquinazoline
• 英文别名: (6,7-dimethoxy-quinazolin-4-yl)-(3-fluoro-4-methyl-phenyl)-amine；N-(3-fluoro-4-methylphenyl)-6,7-dimethoxyquinazolin-4-amine
• CAS: 1268310-02-6
• 化学式: C₁₇H₁₆FN₃O₂
• 分子量: 313.331
• InChiKey: LPHHWGKFRYVWLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氟-4-甲基苯胺 、 4-氯-6,7-二甲氧基喹唑啉 以 乙腈 为溶剂， 反应 24.0h， 以94%的产率得到4-(3-fluoro-4-methylanilino)-6,7-dimethoxyquinazoline
  参考文献：
  名称：

  Investigation of a novel molecular descriptor for the lead optimization of 4-aminoquinazolines as vascular endothelial growth factor receptor-2 inhibitors: Application for quantitative structure–activity relationship analysis in lead optimization

  摘要：

  We investigated the use of infrared vibrational frequency of ligands as a potential novel molecular descriptor in three different molecular target and chemical series. The vibrational energy of a ligand was approximated from the sum of infrared (IR) absorptions of each functional group within a molecule and normalized by its molecular weight (MDIR). Calculations were performed on a set of 4-aminoquinazolines with similar docking scores for the VEGFR2/KDR receptor. 4-Aminoquinazolines with MDIR values ranging 192-196 provided compounds with KDR inhibitory activity. The correlation of KDR inhibitory activity was similarly observed in a separate chemical series, the pyrazolo[1,5-a]pyrimidines. Initial exploration of this molecular descriptor supports a tool for rapid lead optimization in the 4-aminoquinazoline chemical series and a potential method for scaffold hopping in pursuit of new inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.037

文献信息

• Investigation of a novel molecular descriptor for the lead optimization of 4-aminoquinazolines as vascular endothelial growth factor receptor-2 inhibitors: Application for quantitative structure–activity relationship analysis in lead optimization
  作者：Joel K. Kawakami、Yannica Martinez、Brandi Sasaki、Melissa Harris、Wendy E. Kurata、Alan F. Lau

  DOI：10.1016/j.bmcl.2011.01.037

  日期：2011.3

  We investigated the use of infrared vibrational frequency of ligands as a potential novel molecular descriptor in three different molecular target and chemical series. The vibrational energy of a ligand was approximated from the sum of infrared (IR) absorptions of each functional group within a molecule and normalized by its molecular weight (MDIR). Calculations were performed on a set of 4-aminoquinazolines with similar docking scores for the VEGFR2/KDR receptor. 4-Aminoquinazolines with MDIR values ranging 192-196 provided compounds with KDR inhibitory activity. The correlation of KDR inhibitory activity was similarly observed in a separate chemical series, the pyrazolo[1,5-a]pyrimidines. Initial exploration of this molecular descriptor supports a tool for rapid lead optimization in the 4-aminoquinazoline chemical series and a potential method for scaffold hopping in pursuit of new inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.