Substituted N-benzylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial and Photosynthesis-inhibiting Activities.

Katarina Kralova; Matus Pesko; Pavla Paterova; Jiri Kunes; Marek Tauchman; Drahomira Eibinova; Cynthia Carillo; Jan Zitko; Martin Dolezal

doi:10.3390/ecsoc-15-00599

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Substituted N-benzylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial and Photosynthesis-inhibiting Activities.

Katarina Kralova

¹,

Matus Pesko

¹,

Pavla Paterova

²,

Jiri Kunes

³,

Marek Tauchman

³,

Drahomira Eibinova

³,

Cynthia Carillo

³,

Jan Zitko

³,

Martin Dolezal

^{*

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

Published: 31 October 2011 by MDPI in The 15th International Electronic Conference on Synthetic Organic Chemistry session Bioorganic, Medicinal and Natural Products

https://doi.org/10.3390/ecsoc-15-00599

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.

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