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Paper | Regular issue | Vol 91, No. 4, 2015, pp.747-763
Published online, 25th February, 2015
DOI: 10.3987/COM-15-13181
Synthesis and Antibacterial Activity of Novel N-Carboxyalkyl-N-phenyl-2-aminothia(oxa)zole Derivatives

Rita Vaickelioniene, Kristina Mickeviciene, Kazimieras Anusevicius, Jurate Siugzdaite, Kristina Kantminiene, and Vytautas Mickevicius*

*Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, Kaunas LT-50254, Lithuania


N-Phenyl-N-thiocarbamoyl-α- and β-methyl-β-alanines were converted into a series of 1,3-thiazole derivatives by treatment with chloroacetaldehyde and haloketones. The reaction of N-phenyl-N-thiocarbamoyl-β-alanines and N-carbamoyl-N-phenyl-β-alanines with 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloroquinoxaline provided naphthoquinone- and quinoxaline-fused thiazoles and oxazoles, respectively. A number of the synthesized compounds exhibited good antibacterial activity against Staphylococcus aureus and Salmonella enteritidis with MIC and MBC values (62.5 and 125 µg/mL, respectively) which are the same or even lower than those for the antibiotic oxytetracycline.