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Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †

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 synthesiz...

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Autores principales: Kucerova-Chlupacova, Marta, Vyskovska-Tyllova, Veronika, Richterova-Finkova, Lenka, Kunes, Jiri, Buchta, Vladimir, Vejsova, Marcela, Paterova, Pavla, Semelkova, Lucia, Jandourek, Ondrej, Opletalova, Veronika
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273737/
https://www.ncbi.nlm.nih.gov/pubmed/27801810
http://dx.doi.org/10.3390/molecules21111421
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author Kucerova-Chlupacova, Marta
Vyskovska-Tyllova, Veronika
Richterova-Finkova, Lenka
Kunes, Jiri
Buchta, Vladimir
Vejsova, Marcela
Paterova, Pavla
Semelkova, Lucia
Jandourek, Ondrej
Opletalova, Veronika
author_facet Kucerova-Chlupacova, Marta
Vyskovska-Tyllova, Veronika
Richterova-Finkova, Lenka
Kunes, Jiri
Buchta, Vladimir
Vejsova, Marcela
Paterova, Pavla
Semelkova, Lucia
Jandourek, Ondrej
Opletalova, Veronika
author_sort Kucerova-Chlupacova, Marta
collection PubMed
description 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.
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spelling pubmed-62737372018-12-28 Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs † Kucerova-Chlupacova, Marta Vyskovska-Tyllova, Veronika Richterova-Finkova, Lenka Kunes, Jiri Buchta, Vladimir Vejsova, Marcela Paterova, Pavla Semelkova, Lucia Jandourek, Ondrej Opletalova, Veronika Molecules Article 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. MDPI 2016-10-27 /pmc/articles/PMC6273737/ /pubmed/27801810 http://dx.doi.org/10.3390/molecules21111421 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kucerova-Chlupacova, Marta
Vyskovska-Tyllova, Veronika
Richterova-Finkova, Lenka
Kunes, Jiri
Buchta, Vladimir
Vejsova, Marcela
Paterova, Pavla
Semelkova, Lucia
Jandourek, Ondrej
Opletalova, Veronika
Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title_full Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title_fullStr Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title_full_unstemmed Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title_short Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs †
title_sort novel halogenated pyrazine-based chalcones as potential antimicrobial drugs †
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273737/
https://www.ncbi.nlm.nih.gov/pubmed/27801810
http://dx.doi.org/10.3390/molecules21111421
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