title: Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides.
abstract: The synthesis and characterization of a new series of furan-3-carboxamides, from the aromatization of 4-trichloroacetyl-2,3-dihydrofuran to 3-trichloroacetyl furan followed by nucleophilic displacement of the trichloromethyl group or the corresponding carboxylic acid chloride by nitrogen-containing compounds, is presented. Preliminary in vitro antimicrobial activity of the title compounds was assessed against a panel of microorganisms including yeast, filamentous fungi, bacteria, and alga. Some of the furan-3-carboxamides exhibited significant in vitro antimicrobial activity. QSAR investigation was applied to find a correlation between the different physicochemical parameters of the compounds studied and their biological activity.
authors.affiliation: Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.015-900, Santa Maria, RS, Brazil. zanatta@base.ufsm.br
authors.forename: Nilo
authors.initials: N
authors.lastname: Zanatta
authors.forename: Sydney H
authors.initials: SH
authors.lastname: Alves
authors.forename: Helena S
authors.initials: HS
authors.lastname: Coelho
authors.forename: Deise M
authors.initials: DM
authors.lastname: Borchhardt
authors.forename: Pablo
authors.initials: P
authors.lastname: Machado
authors.forename: Kelen M
authors.initials: KM
authors.lastname: Flores
authors.forename: Fabio M
authors.initials: FM
authors.lastname: da Silva
authors.forename: Tatiana B
authors.initials: TB
authors.lastname: Spader
authors.forename: Jânio M
authors.initials: JM
authors.lastname: Santurio
authors.forename: Helio G
authors.initials: HG
authors.lastname: Bonacorso
authors.forename: Marcos A P
authors.initials: MA
authors.lastname: Martins
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000145:classification / Q000187:drug effects; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D021281:Quantitative Structure-Activity Relationship; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000577:Amides; D000935:Antifungal Agents; D005663:Furans