Microwave-Assisted Synthesis and Biological Activities of 3,6-Disubstituted-1,2,4-triazine Derivatives

doi:10.6023/cjoc201304011

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2178-2185.DOI: 10.6023/cjoc201304011 Previous Articles Next Articles

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3,6-二取代-1,2,4-三嗪衍生物的微波辅助合成及生物活性

李英俊^a, 邵昕^a, 高立信^b, 靳焜^c, 盛丽^b, 罗潼川^a, 于洋^a, 李佳^b

a 辽宁师范大学化学化工学院大连 116029;
b 中国科学院上海药物研究所国家新药筛选中心药物研究国家重点实验室上海 201203;
c 大连理工大学精细化工国家重点实验室大连 116012

收稿日期:2013-04-08 修回日期:2013-05-14 发布日期:2013-06-21
通讯作者: 李英俊, 李佳 E-mail:chemlab.lnnu@163.com
基金资助:
辽宁省自然科学基金(No. 20102126)资助项目

Microwave-Assisted Synthesis and Biological Activities of 3,6-Disubstituted-1,2,4-triazine Derivatives

Li Yingjun^a, Shao Xin^a, Gao Lixin^b, Jin Kun^c, Sheng Li^b, Luo Tongchuan^a, Yu Yang^a, Li Jia^b

a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
b National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Received:2013-04-08 Revised:2013-05-14 Published:2013-06-21
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

Twenty new 3,6-disubstituted-1,2,4-triazine derivatives containing benzimidazole moiety (4) were synthesized via microwave-assisted condensation reactions of 2-aryloxymethylbenzimidazole-1-acetylhydrazines (3) with various (un)substituted phenacyl bromides in DMF. The structures were characterized by IR, ¹H NMR spectra and elemental analysis. The optimum experimental conditions were found. Compared with traditional methods, this synthetic method has such advantages as short reaction time, simple operation, broad substrate scope, easy purification and high yields. The synthesized target compounds were screened for Cdc25B and PTP1B inhibitory activities. The experimental results indicate that compounds 4g and 4j showed good inhibitory activities against Cdc25B, and 4a, 4h, 4j, 4r and 4s exhibited potent inhibitory activities against PTP1B. It is noteworthy that compound 4j can be used as potential Cdc25B and PTP1B inhibitors in the treatment of cancer and diabetes.

Key words: microwave irradiation, 1,2,4-triazines, benzimidazole, synthesis, Cdc25B and PTP1B inhibitors

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Li Yingjun, Shao Xin, Gao Lixin, Jin Kun, Sheng Li, Luo Tongchuan, Yu Yang, Li Jia. Microwave-Assisted Synthesis and Biological Activities of 3,6-Disubstituted-1,2,4-triazine Derivatives[J]. Chin. J. Org. Chem., 2013, 33(10): 2178-2185.

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3,6-二取代-1,2,4-三嗪衍生物的微波辅助合成及生物活性

Microwave-Assisted Synthesis and Biological Activities of 3,6-Disubstituted-1,2,4-triazine Derivatives

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