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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 5: 1266 - 1274

DOI: https://doi.org/10.6023/cjoc201908007

Synthesis and Biological Evaluation of Polysubstituted 5-Amino-3,7-diphenyl-7H-thiazolo[3,2-a]pyrimidine-6-carbonitriles

  • Ren Xuanxuan ,
  • Yuan Rui ,
  • Chen Wen ,
  • Zhou Hang ,
  • Ye Fei ,
  • Shi Xueying ,
  • Hu Juan ,
  • Zhang Peng ,
  • Zhou Shengliang ,
  • Wan Yu ,
  • Wu Hui
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  • a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
    b Key Laboratory of Biotechnology for Medicinal Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
    c School of Life Science, Jiangsu Normal University, Xuzhou 221116

Received date: 2019-08-05

  Revised date: 2019-10-22

  Online published: 2020-02-15

Supported by

Project supported by the Priority Academic Program Development of Jiangsu Higher Education Institutions (Third Period), the Natural Science Research Projects in Universities of Jiangsu Provinc(No. 19KJB430019), the Science and Technology Foundation of Xuzhou City (No. KC19242), the Aid Project for Ph.D. Faculties in Jiangsu Normal University (No. 17XLR023) and the Graduate Student Scientific Research Innovation Projects in Jiangsu Province (Nos. KYCX18_2111,KYCX18_2116).

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Abstract

A series of thiazolo[3,2-a]pyrimidine derivatives were synthesized from the reaction of α-bromoacetophenone, aromatic aldehyde, malononitrile and thiourea which was catalyzed by Tröger's base derivative 5,12-dimethyl-3,10-diphenyl- bis-1H-pyrazol[b,f] [4,5]-1,5- diazadicyclo[3.3.1]-2,6-octadiene (1). The reaction mechanism was discussed by the 1H NMR analysis and chemical experiments. The pharmacological activity results of the products indicated that most of products showed high inhibitory on one or more cancer cells in human hepatocarcinoma cell (HepG2), human non-small cell lung cancer cell (247) and human non-small cell lung cancer cell (A549) in vitro. And seven products have antibacterial activity against the methicillin-resistant Staphylococcus aureus. These results showed the great potential of these compounds in drug development.

Key words： Tröger's base derivative; catalysis; thiazolo[3,2-a]pyrimidine derivative; anti-tumor; anti-bacterial

Cite this article

Ren Xuanxuan , Yuan Rui , Chen Wen , Zhou Hang , Ye Fei , Shi Xueying , Hu Juan , Zhang Peng , Zhou Shengliang , Wan Yu , Wu Hui . Synthesis and Biological Evaluation of Polysubstituted 5-Amino-3,7-diphenyl-7H-thiazolo[3,2-a]pyrimidine-6-carbonitriles[J]. Chinese Journal of Organic Chemistry, 2020 , 40(5) : 1266 -1274 . DOI: 10.6023/cjoc201908007

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