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Chinese Journal of Organic Chemistry >

2015 , Vol. 35 >Issue 1: 191 - 199

DOI: https://doi.org/10.6023/cjoc201405032

Articles

Synthesis, Characterization and Biological Activities of 3,5,6-Trisubstituted-1,2,4-triazine Derivatives

  • Li Yingjun ,
  • Shi Xiangling ,
  • Gao Lixin ,
  • Jin Kun ,
  • Sheng Li ,
  • Wu Jianghong ,
  • Peng Lina ,
  • Li Jia
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  • a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b State Key Laboratory of Drug Research, National Center for Drug Screening, 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 date: 2014-05-21

  Revised date: 2014-07-25

  Online published: 2014-09-09

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Abstract

Thirty new 3,5,6-trisubstituted-1,2,4-triazine derivatives containing benzimidazole moiety (5～6) were synthesized via microwave-assisted condensation reactions of 2-aryloxymethylbenzimidazole-1-acetylhydrazines (3) with benzil/p-anisil in the presence of NH4OAc/HOAc. The structures were characterized by elemental analysis, IR, 1H NMR spectra and single crystal X-ray determination. The synthesized target compounds were evaluated for Cdc25B and PTP1B inhibitory activities. The structure-activity relationship (SAR) was also briefly discussed. The experimental results indicated that some compounds showed good inhibitory activities against Cdc25B and PTP1B. Among of them, compound 6o [IC50=(0.84±0.22) μg/mL] exhibited highest inhibitory activity against Cdc25B. Compounds 5i, 5m, 5n, 6h, 6j, 6m, 6n and 6o showed higher inhibitory activities against PTP1B [IC50=(0.46±0.10)～(0.87±0.19) μg/mL] than positive control oleanolic acid [IC50=(0.97±0.15) μg/mL]. It is noteworthy that, compounds 5h, 5m, 6n and 6o showed inhibitory activities against Cdc25B and PTP1B. The target compounds can be considered as potential Cdc25B and PTP1B inhibitors.

Key words： 3,5,6-trisubstituted-1,2,4-triazine; benzimidazole; microwave irradiation; synthesis; crystal structure; Cdc25B and PTP1B inhibitors

Cite this article

Li Yingjun , Shi Xiangling , Gao Lixin , Jin Kun , Sheng Li , Wu Jianghong , Peng Lina , Li Jia . Synthesis, Characterization and Biological Activities of 3,5,6-Trisubstituted-1,2,4-triazine Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 191 -199 . DOI: 10.6023/cjoc201405032

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