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Molecules 2016, 21(11), 1421; doi:10.3390/molecules21111421

Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

1
Department of Pharmaceutical Chemistry and Pharmaceutical Analysis, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
2
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
3
Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
4
Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic
Preliminary Results were Presented at the 8th Central European Conference “Chemistry towards Biology” (CTB-2016), Brno, Czech Republic, 28 August–1 September 2016 (Paper P-38).
*
Author to whom correspondence should be addressed.
Academic Editor: Josef Jampilek
Received: 23 September 2016 / Revised: 14 October 2016 / Accepted: 14 October 2016 / Published: 27 October 2016
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Abstract

Chalcones, i.e., compounds with the chemical pattern of 1,3-diphenylprop-2-en-1-ones, exert a wide range of bio-activities, e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc. Our research group has been focused on pyrazine analogues of chalcones; several series have been synthesized and tested in vitro on antifungal and antimycobacterial activity. The highest potency was exhibited by derivatives with electron withdrawing groups (EWG) in positions 2 and 4 of the ring B. As halogens also have electron withdrawing properties, novel halogenated derivatives were prepared by Claisen-Schmidt condensation. All compounds were submitted for evaluation of their antifungal and antibacterial activity, including their antimycobacterial effect. In the antifungal assay against eight strains of selected fungi, growth inhibition of Candida glabrata and Trichophyton interdigitale (formerly T. mentagrophytes) was shown by non-alkylated derivatives with 2-bromo or 2-chloro substitution. In the panel of selected bacteria, 2-chloro derivatives showed the highest inhibitory effect on Staphylococcus sp. In addition, all products were also screened for their antimycobacterial activity against Mycobacterium tuberculosis H37RV My 331/88, M. kansasii My 235/80, M. avium 152/80 and M. smegmatis CCM 4622. Some of the examined compounds, inhibited growth of M. kansasii and M. smegmatis with minimum inhibitory concentrations (MICs) comparable with those of isoniazid. View Full-Text
Keywords: pyrazine; chalcone; halogenated; antifungal; antibacterial; antimycobacterial pyrazine; chalcone; halogenated; antifungal; antibacterial; antimycobacterial
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Kucerova-Chlupacova, M.; Vyskovska-Tyllova, V.; Richterova-Finkova, L.; Kunes, J.; Buchta, V.; Vejsova, M.; Paterova, P.; Semelkova, L.; Jandourek, O.; Opletalova, V. Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs. Molecules 2016, 21, 1421.

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