title: Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs.
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 ofCandida glabrataandTrichophyton interdigitale(formerlyT. 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 onStaphylococcussp. In addition, all products were also screened for their antimycobacterial activity againstMycobacterium tuberculosisH37RV My 331/88,M. kansasiiMy 235/80,M. avium152/80 andM. smegmatisCCM 4622. Some of the examined compounds, inhibited growth ofM. kansasiiandM. smegmatiswith minimum inhibitory concentrations (MICs) comparable with those of isoniazid.
authors: 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. kucerom@faf.cuni.cz.
authors: Marta
authors: M
authors: Kucerova-Chlupacova
authors: 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. good-message@seznam.cz.
authors: Veronika
authors: V
authors: Vyskovska-Tyllova
authors: 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. lenka.finkova@seznam.cz.
authors: Lenka
authors: L
authors: Richterova-Finkova
authors: Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. kunes@faf.cuni.cz.
authors: Jiri
authors: J
authors: Kunes
authors: Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. vejsova@faf.cuni.cz.|Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic. vejsova@faf.cuni.cz.
authors: Vladimir
authors: V
authors: Buchta
authors: Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. vladimir.buchta@fnhk.cz.|Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic. vladimir.buchta@fnhk.cz.
authors: Marcela
authors: M
authors: Vejsova
authors: Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. pavla.paterova@fnhk.cz.|Department of Clinical Microbiology, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic. pavla.paterova@fnhk.cz.
authors: Pavla
authors: P
authors: Paterova
authors: 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. semelkol@faf.cuni.cz.
authors: Lucia
authors: L
authors: Semelkova
authors: 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. jando6aa@faf.cuni.cz.
authors: Ondrej
authors: O
authors: Jandourek
authors: 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. opletalova@faf.cuni.cz.
authors: Veronika
authors: V
authors: Opletalova
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D041221:Candida glabrata / Q000254:growth & development*; D002599:Chalcone / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009161:Mycobacterium / Q000254:growth & development*; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014249:Trichophyton / Q000254:growth & development*
chemical_list: D000890:Anti-Infective Agents; D006846:Hydrocarbons, Halogenated; D011719:Pyrazines; D002599:Chalcone
keywords: antibacterial; antifungal; antimycobacterial; chalcone; halogenated; pyrazine