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Substituted N-benzylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial and Photosynthesis-inhibiting Activities.
1 , 1 , 2 , 3 , 3 , 3 , 3 , 3 , * 3
1  Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska Dolina Ch-2, 84215 Bratislava, Slovakia
2  Department of Clinical Microbiology, Charles University Medical School and Teaching Hospital, Sokolska 581, Hradec Kralove 500 05, Czech Republic
3  Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, 500 05 Hradec Králové, Czech Republic

Abstract: This communication deals with the synthesis and evaluation of some pyrazinamide (PZA) analogues/prodrugs. A series of sixteen pyrazinamide analogues with the –CO-NH-CH2- or -NH-CH2- linkers connecting the pyrazine and benzene rings was prepared by using the microwave assisted coupling reaction of substituted methyl-pyrazinecarboxylate with ring-substituted benzylamines and characterized. The results of in vitro antimycobacterial screening indicated some interesting antimycobacterial activity in the series of N-benzylpyrazine-2-carboxamides. From the second series, 3-(3,4-dichlorobenzylamino)pyrazine-2-carboxamide was the most active in the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts (IC50 = 2.2 μmol mL-1).
Keywords: Pyrazinecarboxamides; Microwave assisted synthesis; Lipophilicity; In vitro antimycobacterial activity; Spinach chloroplasts; PET inhibition; Structure-activity relationships.