EventsThe 15th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-15-00599
This submission belongs to the session b. Bioorganic, Medicinal and Natural Products of the event The 15th International Electronic Conference on Synthetic Organic Chemistry
Published date
31 Oct, 2011
Citation
Katarina Kralova, Matus Pesko, Pavla Paterova, Jiri Kunes, Marek Tauchman, Drahomira Eibinova, Cynthia Carillo, Jan Zitko, Martin Dolezal, Substituted N-benzylpyrazine-2-carboxamides, Their Synthesis, Hydro-lipophilic Properties and Evaluation of Their Antimycobacterial and Photosynthesis-inhibiting Activities., in Proceedings of The 15th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2011, MDPI: Basel, Switzerland, 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
image
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
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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