2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile | 1128018-66-5

• 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: 2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile
• CAS: 1128018-66-5
• 化学式: C₉H₄ClF₂N₅
• 分子量: 255.614
• InChiKey: HUFZFQIKKOHBPR-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  531.9±60.0 °C(predicted)
• 密度：
  1.73±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丙烷-1-硫醇 、 2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以73%的产率得到2,4-diamino-8-chloro-5,7-bis(propylthio)quinazoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents

  摘要：

  Novel polyhalo 2,4-diaminoquinazolines 3a-3d were prepared by reacting polyhaloisophthalonitriles with guanidine carbonate under solvent-free conditions and in the absence of a catalyst with good yields (74-95%). A series of highly functionalized 2,4-diaminoquinazolines 4-5 were then synthesized based on 3a-3c. The anticancer activities of compounds 3-5 were evaluated in vitro against human cell lines such as Skov-3, HL-60, A431, A549, and HepG-2. Some of the compounds showed excellent cytotoxic activity and 5a was found to be the most potent derivative, with an IC50 value lower than 2.5 mu g/mL against the five tumor cell lines, making it more active than cisplatin. Representative compounds were also preliminarily evaluated as HIV-1 inhibitors in vitro, and 3c showed the most potent anti-HIV-1 activity with EC50 values of 0.6 and 1.6 mu g/mL, and TI values of >59.6 and 66.6, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.056
• 作为产物：
  描述：

  5-氯-2,4,6-三氟间苯二甲腈 、 碳酸胍 反应 0.17h， 以92%的产率得到2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents

  摘要：

  Novel polyhalo 2,4-diaminoquinazolines 3a-3d were prepared by reacting polyhaloisophthalonitriles with guanidine carbonate under solvent-free conditions and in the absence of a catalyst with good yields (74-95%). A series of highly functionalized 2,4-diaminoquinazolines 4-5 were then synthesized based on 3a-3c. The anticancer activities of compounds 3-5 were evaluated in vitro against human cell lines such as Skov-3, HL-60, A431, A549, and HepG-2. Some of the compounds showed excellent cytotoxic activity and 5a was found to be the most potent derivative, with an IC50 value lower than 2.5 mu g/mL against the five tumor cell lines, making it more active than cisplatin. Representative compounds were also preliminarily evaluated as HIV-1 inhibitors in vitro, and 3c showed the most potent anti-HIV-1 activity with EC50 values of 0.6 and 1.6 mu g/mL, and TI values of >59.6 and 66.6, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.056

文献信息

• Synthesis of highly functionalized 2,4-diaminoquinazolines as anticancer and anti-HIV agents
  作者：Sheng-Jiao Yan、Han Zheng、Chao Huang、Yu-Yun Yan、Jun Lin

  DOI：10.1016/j.bmcl.2010.06.056

  日期：2010.8

  Novel polyhalo 2,4-diaminoquinazolines 3a-3d were prepared by reacting polyhaloisophthalonitriles with guanidine carbonate under solvent-free conditions and in the absence of a catalyst with good yields (74-95%). A series of highly functionalized 2,4-diaminoquinazolines 4-5 were then synthesized based on 3a-3c. The anticancer activities of compounds 3-5 were evaluated in vitro against human cell lines such as Skov-3, HL-60, A431, A549, and HepG-2. Some of the compounds showed excellent cytotoxic activity and 5a was found to be the most potent derivative, with an IC50 value lower than 2.5 mu g/mL against the five tumor cell lines, making it more active than cisplatin. Representative compounds were also preliminarily evaluated as HIV-1 inhibitors in vitro, and 3c showed the most potent anti-HIV-1 activity with EC50 values of 0.6 and 1.6 mu g/mL, and TI values of >59.6 and 66.6, respectively. (C) 2010 Elsevier Ltd. All rights reserved.