Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1266-1274.DOI: 10.6023/cjoc201908007 Previous Articles     Next Articles

多取代-5-氨基-3,7-二苯基-7H-噻唑并[3,2-a]嘧啶-6-腈衍生物的合成及生物活性

任璇璇a, 苑睿b, 陈雯a, 周杭a, 叶菲a, 师雪荧a, 胡娟a, 张鹏c, 周生亮b, 宛瑜b, 吴翚b   

  1. a 江苏师范大学化学与材料科学学院 江苏徐州 221116;
    b 江苏师范大学江苏省药用植物生物技术重点实验室 江苏徐州 221116;
    c 江苏师范大学生命科学学院 江苏徐州 221116
  • 收稿日期:2019-08-05 修回日期:2019-10-22 出版日期:2020-05-25 发布日期:2020-02-15
  • 通讯作者: 宛瑜, 吴翚 E-mail:wuhui72@jsnu.edu.cn;853270845@qq.com
  • 基金资助:
    江苏省高校优势学科建设工程(三期)、江苏省高校自然科学研究面上项目(No.19KJB430019)、徐州市科技计划项目(No.KC19242)、江苏师范大学博士学位教师科研支持项目(No.17XLR023)和江苏省研究生创新计划(Nos.KYCX18_2111,KYCX18_2116)资助项目.

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

Ren Xuanxuana, Yuan Ruib, Chen Wena, Zhou Hanga, Ye Feia, Shi Xueyinga, Hu Juana, Zhang Pengc, Zhou Shengliangb, Wan Yub, Wu Huib   

  1. 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:2019-08-05 Revised:2019-10-22 Online:2020-05-25 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).

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