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...

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Bibliographic Details
Published in:	Bioorganic & medicinal chemistry Vol. 15; no. 5; pp. 1947 - 1958
Main Authors:	Zanatta, Nilo, Alves, Sydney H., Coelho, Helena S., Borchhardt, Deise M., Machado, Pablo, Flores, Kelen M., da Silva, Fabio M., Spader, Tatiana B., Santurio, Jânio M., Bonacorso, Helio G., Martins, Marcos A.P.
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Ltd 01-03-2007 Elsevier Science
Subjects:	Amides - chemical synthesis Amides - chemistry Amides - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antimicrobial activity Biological and medical sciences Fungi - classification Fungi - drug effects Furan Furan-3-carboxamides Furans - chemistry General aspects Magnetic Resonance Spectroscopy Medical sciences MIC Microbial Sensitivity Tests Minimal inhibitory concentration Models, Molecular Pharmacology. Drug treatments QSAR Quantitative Structure-Activity Relationship Spectrometry, Mass, Electrospray Ionization Trichloroacetyl furan Furan Minimal inhibitory concentration Antimicrobial activity Furan-3-carboxamides QSAR MIC Trichloroacetyl furan Five membered ring Prediction Oxygen heterocycle In vitro Antimicrobial agent Antifungal agent Structure activity relation Antibacterial agent Chemical synthesis
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2007.01.003