Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides.
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.
Zanatta
Nilo
N
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
Alves
Sydney H
SH
Coelho
Helena S
HS
Borchhardt
Deise M
DM
Machado
Pablo
P
Flores
Kelen M
KM
da Silva
Fabio M
FM
Spader
Tatiana B
TB
Santurio
Jânio M
JM
Bonacorso
Helio G
HG
Martins
Marcos A P
MA
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
D000577:Amides; D000935:Antifungal Agents; D005663:Furans