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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1468-1472.DOI: 10.6023/cjoc201203003 上一篇    下一篇

研究论文

新型2-氨基-呋喃并[2,3-d]嘧啶-4(3H)-酮衍生物的合成及抗肿瘤活性

胡扬根a,b, 高海涛b, 王刚a, 王燕c, 屈永年b, 徐靖b   

  1. a 湖北医药学院附属太和医院药学部 十堰 442000;
    b 湖北医药学院医学化学研究所 十堰 442000;
    c 湖北医药学院基础医学研究所 十堰 442000
  • 收稿日期:2012-03-20 修回日期:2012-04-11 发布日期:2012-04-17
  • 通讯作者: 胡扬根, 徐靖 E-mail:huyangg111@yahoo.com.cn;jxu6686@yahoo.com.cn
  • 基金资助:

    湖北省科技厅自然科学基金(No. 2011CDB08301)、湖北省教育厅研究(Nos. D20092406, Q20102110)和湖北医药学院优秀中青年科技创新团队研究(Nos. 2011CXX03, 2009QDJ15)资助项目.

Synthesis and Antitumor Activity of Some 2-Amino-furo[2,3-d]- yrimidin-4(3H)-one Derivatives

Hu Yanggena,b, Gao Haitaob, Wang Ganga, Wang Yanc, Qu Yongnianb, Xu Jingb   

  1. a Department of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000;
    b Institute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000;
    c Institute of Basic Medical Sciences, Hubei University of Medicine, Shiyan 442000
  • Received:2012-03-20 Revised:2012-04-11 Published:2012-04-17
  • Supported by:

    Project supported by the Natural Science Foundation of Hubei Provincial Department of Science and Technology (No. 2011CDB08301), the Science Research Project of Hubei Provincial Department of Education (Nos. D20092406, Q20102110) and the Science and Technology Innovation Team Project of Hubei University of Medicine (Nos. 2011CXX03, 2009QDJ15).

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报道应用aza-Wittig反应, 采用易得的原料, 在温和的条件下, 以78%～90%的产率有效的合成了新型2-氨基-呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物5, 其结构经IR, 1H NMR, MS和元素分析确认. 为进一步得到结构确认, 化合物5c经X射线衍射分析证实. 运用噻唑蓝(MTT)标准法对化合物5进行了体外抗肿瘤活性的测定, 其中5f对肺癌细胞A459的IC50值为18.4 mmol/L, 显示出潜在良好的抗肿瘤活性.

关键词: 呋喃并[2,3-d]嘧啶-4(3H)-酮, 合成, 抗肿瘤活性

In this paper, a novel series of 2-aminofuro[2,3-d]yrimidin-4(3H)-one derivatives were prepared via aza-Wittig reaction of iminophosphorane 3 with aromatic isocyanate and subsequent reaction with various amine under mild condition in 78%～90% yields. The structures of these compounds were confirmed by mass spectral data, 1H NMR, IR and elemental analysis. Compound 5c was further analyzed by single crystal X-ray diffraction. The in vitro antitumor activities of compounds 5 were analyzed with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide (MTT) standard method, and compound 5f showed the best inhibition activities against A459 with IC50 18.4 mmol/L.

Key words: furo[2,3-d]pyrimidin-4(3H)-one, synthesis, antitumor activity