Čes. slov. farm. 2015, 64(1):19-24 | DOI: 10.36290/csf.2015.004

Synthesis and anti-infective evaluation of 5-amino-N-phenylpyrazine-2-carboxamides

Jan Zitko^1,*, Fernando Franco¹, Pavla Paterová²

¹ Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University in Prague, Hradec Králové, Czech Republic

² Department of Clinical Microbiology, University Hospital, Hradec Králové, Czech Republic

A series of eleven novel 5-amino-N-phenylpyrazine-2-carboxamides were synthesized and evaluated for in vitro anti-infective properties. Prepared compounds were characterized by IR, ¹H NMR and ¹³C NMR spectra, elementary analysis and melting points. Lipophilicity parameters Log P and ClogP were calculated. None of the compounds was effective against any of tested mycobacterial strains (Mycobacterium tuberculosis H37Rv, M. kansasii, M. avium) up to concentration of 100 μg/mL. 5-amino-N-(2,5-dimethylphenyl) pyrazine-2-carboxamide (

3) exerted moderate antibacterial activity against Staphylococcus aureus (MIC = 62.5 μM). No antifungal activity was detected. Several compounds exerted moderate antiviral activity against influenza A viruses at the level of tens of μM.

Keywords: pyrazinamide; antimycobacterial activity; antibacterial activity; antifungal activity; antiviral activity

Grants and funding:

This work was financially supported by IGA NT 13346 and SVV 260 183. Authors wish to thank Ida Dufková for performing in vitro antifungal and antibacterial screening and Assoc. Professor Lieve Naesens (Rega Institute for Medical Research, Laboratory of Virology and Chemotherapy, Leuven, Belgium) for coordination of antiviral testing.

Received: February 27, 2015; Accepted: March 24, 2015; Published: January 1, 2015  Show citation