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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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-03, Vol.15 (5), p.1947-1958 |
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| container_end_page | 1958 |
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| container_issue | 5 |
| container_start_page | 1947 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 15 |
| creator | 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. |
| description | 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. |
| doi_str_mv | 10.1016/j.bmc.2007.01.003 |
| format | Article |
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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.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.01.003</identifier><identifier>PMID: 17240153</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>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. 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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.</description><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Biological and medical sciences</subject><subject>Fungi - classification</subject><subject>Fungi - drug effects</subject><subject>Furan</subject><subject>Furan-3-carboxamides</subject><subject>Furans - chemistry</subject><subject>General aspects</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>MIC</subject><subject>Microbial Sensitivity Tests</subject><subject>Minimal inhibitory concentration</subject><subject>Models, Molecular</subject><subject>Pharmacology. 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| ispartof | Bioorganic & medicinal chemistry, 2007-03, Vol.15 (5), p.1947-1958 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| 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 |
| title | Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides |
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