2-chloro-N-(4-fluorophenyl)quinazolin-4-amine

• 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-chloro-N-(4-fluorophenyl)quinazolin-4-amine
• 化学式: C₁₄H₉ClFN₃
• mdl: MFCD09726647
• 分子量: 273.697
• InChiKey: FTDWYVGZHYGGTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-fluorophenyl)quinazolin-4-amine 、 4-甲苯硼酸 在 NHC-Pd(II)-Im 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以97%的产率得到N-(4-fluorophenyl)-2-(4-methylphenyl)quinazolin-4-amine
  参考文献：
  名称：

  N-heterocyclic carbene-Pd(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of 2-chloro-4-aminoquinazolines with arylboronic acids

  摘要：

  The Suzuki-Miyaura coupling between 2-chloro-4-aminoquinazolines and arylboronic acids catalyzed by the well-defined N-heterocyclic carbene-PdCl2-1-methylimidazole complex was performed at room temperature, giving the desired products in good to high yields. Through this methodology, a variety of 2-aryl-4-aminoquinazoline derivatives with potential pharmaceutical activities can be achieved under mild reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131548
• 作为产物：
  描述：

  2,4-喹唑啉二酮 在 三正丙胺 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 2-chloro-N-(4-fluorophenyl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold

  摘要：

  A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a K-i value of 14.04 +/- 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D-1 and D-2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.030

文献信息

• N-heterocyclic carbene-Pd(II)-1-methylimidazole complex-catalyzed Suzuki-Miyaura coupling of 2-chloro-4-aminoquinazolines with arylboronic acids
  作者：Zhen Bao、Zhi-Yuan Zhou、Ye-Ting Mao、Li-Xiong Shao

  DOI：10.1016/j.tet.2020.131548

  日期：2020.10

  The Suzuki-Miyaura coupling between 2-chloro-4-aminoquinazolines and arylboronic acids catalyzed by the well-defined N-heterocyclic carbene-PdCl2-1-methylimidazole complex was performed at room temperature, giving the desired products in good to high yields. Through this methodology, a variety of 2-aryl-4-aminoquinazoline derivatives with potential pharmaceutical activities can be achieved under mild reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.
• Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold
  作者：Xinxian Deng、Lin Guo、Lili Xu、Xuechu Zhen、Kunqian Yu、Weili Zhao、Wei Fu

  DOI：10.1016/j.bmcl.2015.07.030

  日期：2015.9

  A series of compounds with quinazoline scaffold were designed, synthesized and evaluated as novel potent 5-HT2A receptor ligands. N-(4-Chlorophenyl)-2-(piperazin-1-yl)quinazolin-4-amine (5o) has a K-i value of 14.04 +/- 0.21 nM, with a selectivity more than 10,000 fold over 5-HT1A receptors (D-1 and D-2-like receptors). The functional assay showed that this compound is an antagonist to 5-HT2A receptor with an IC50 value of 1.66 mu M. (C) 2015 Elsevier Ltd. All rights reserved.