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

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-diphenylbis-1H-pyrazol[b,f][4,5]-1,5diazadicyclo[3.3.1]-2,6-octadiene (1). The reaction mechanism was discussed by the H 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.