title: Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes.
abstract: Drug resistance has become a major concern in the field of infection management, therefore searching for new antibacterial agents is getting more challenging. Our study presents an optimized and eco-friendly synthesis scheme for a panel of nitroalkenes bearing various functional groups in the aromatic moiety and bromine or cyano substituents in 1 position of nitrovinyl moiety. The presence of nitrolefine group outside the ring minimalizes genotoxic properties while conjugation of aryl group with nitrovinyl moiety increases stability of the compounds. Then our research focused on evaluation of biological properties of such obtained (E)-2-aryl-1-cyano-1-nitroethenes. As they exhibit strong bacteriostatic and bactericidal activities against reference bacteria and yeast species with no detectable cytotoxicity towards cultured human HepG2 and HaCaT cells, they could be promising candidates for the replacement of traditional nitrofurane-containing antibacterial drugs. Nevertheless, validation of the obtained data in an in vivo model and additional safety studies on mutagenicity are still required.
authors.affiliation: a Department of Medical Chemistry, Faculty of Medicine , Medical University of Lublin , Lublin , Poland .
authors.forename: Anna
authors.initials: A
authors.lastname: Boguszewska-Czubara
authors.affiliation: b Institute of Organic Chemistry and Technology, Cracov University of Technology , Cracov , Poland .
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Lapczuk-Krygier
authors.affiliation: b Institute of Organic Chemistry and Technology, Cracov University of Technology , Cracov , Poland .
authors.forename: Konrad
authors.initials: K
authors.lastname: Rykala
authors.affiliation: c Department of Pharmaceutical Microbiology .
authors.forename: Anna
authors.initials: A
authors.lastname: Biernasiuk
authors.affiliation: d Department of Biopharmacy , and.
authors.forename: Artur
authors.initials: A
authors.lastname: Wnorowski
authors.affiliation: e Department of Organic Chemistry, Faculty of Pharmacy , Medical University of Lublin , Lublin , Poland.
authors.forename: Lukasz
authors.initials: L
authors.lastname: Popiolek
authors.affiliation: a Department of Medical Chemistry, Faculty of Medicine , Medical University of Lublin , Lublin , Poland .
authors.forename: Agata
authors.initials: A
authors.lastname: Maziarka
authors.affiliation: a Department of Medical Chemistry, Faculty of Medicine , Medical University of Lublin , Lublin , Poland .
authors.forename: Anna
authors.initials: A
authors.lastname: Hordyjewska
authors.affiliation: b Institute of Organic Chemistry and Technology, Cracov University of Technology , Cracov , Poland .
authors.forename: Radomir
authors.initials: R
authors.lastname: Jasiński
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival; D002478:Cells, Cultured; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D056945:Hep G2 Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D009570:Nitriles; D009574:Nitro Compounds
keywords: Biological activity; Gram-positive and Gram-negative bacteria; cytotoxicity; fungicide; ionic liquids; minimal bactericidal concentration