2,4-diamino-8-chloro-5-fluoro-7-(phenylamino)quinazoline-6-carbonitrile | 1128018-37-0

• 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-fluoro-7-(phenylamino)quinazoline-6-carbonitrile
• 英文别名: 2,4-Diamino-7-anilino-8-chloro-5-fluoro-quinazoline-6-carbonitrile；2,4-diamino-7-anilino-8-chloro-5-fluoroquinazoline-6-carbonitrile
• CAS: 1128018-37-0
• 化学式: C₁₅H₁₀ClFN₆
• 分子量: 328.736
• InChiKey: HJFOCKVOKIPCRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 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：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-diamino-8-chloro-5,7-difluoroquinazoline-6-carbonitrile 、 苯胺 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以61%的产率得到2,4-diamino-8-chloro-5-fluoro-7-(phenylamino)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

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.