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Substituted N-benzylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial and Photosynthesis-inhibiting Activities.
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Published:
31 October 2011
by MDPI
in The 15th International Electronic Conference on Synthetic Organic Chemistry
session Bioorganic, Medicinal and Natural Products
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.
