Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs.

Marcela Vejsova,Jiri Kunes,Pavla Paterova,Veronika Opletalova,Marta Kucerova-Chlupacova,Veronika Vyskovska-Tyllova,Vladimir Buchta,Lucia Semelkova,Ondrej Jandourek,Lenka Richterova-Finkova

doi:10.3390/molecules21111421

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.

Highlights

Chalcones are compounds with the basic scaffold of 1,3-diphenylprop-2-en-1-one, containing ringA and ring B connected by an α,β-unsaturated keto linker.Naturally-occurring chalcones usually bear hydroxy, methoxy- or prenylMolecules 2016, 21, 1421; doi:10.3390/molecules21111421 www.mdpi.com/journal/molecules substitutions and might serve as precursors of other flavonoid groups
Inchalcones, synthetic chalcones, substitutents can bevaried more varied and benzene been many times replaced with other aryls or heteroaryls rings have been many times replaced with other aryls or heteroaryls [2,3]
We report the results of its antibacterial testing and its effects on the growth of other mycobacteria

Summary

Introduction

Chalcones are compounds with the basic scaffold of 1,3-diphenylprop-2-en-1-one, containing ring. Molecules 2016, 21, 1421; doi:10.3390/molecules21111421 www.mdpi.com/journal/molecules substitutions and might serve as precursors of other flavonoid groups. Chalcones exert a wide range substitutions and might serve as precursors of other flavonoid groups. Chalcones exert a wide range of bio-activities (e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc.), which were several of bio-activities (e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc.), which were times reviewed [1,2,3]. In synthetic substitutents can be more and benzene rings have several times reviewed [1,2,3]. Inchalcones, synthetic chalcones, substitutents can bevaried more varied and benzene been many times replaced with other aryls or heteroaryls [2,3]

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Conclusion