Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives
A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) w...
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MDPI AG
2018-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/1/199 |
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doaj-4637e6112b1a4c40b78c53b7451caecb2020-11-24T22:04:11ZengMDPI AGMolecules1420-30492018-01-0123119910.3390/molecules23010199molecules23010199Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin DerivativesPriscila López-Rojas0Monika Janeczko1Konrad Kubiński2Ángel Amesty3Maciej Masłyk4Ana Estévez-Braun5Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206 La Laguna, Tenerife, SpainDepartment of Molecular Biology, The John Paul II Catholic University of Lublin, ul. Konstantynów 1i, 20-708 Lublin, PolandDepartment of Molecular Biology, The John Paul II Catholic University of Lublin, ul. Konstantynów 1i, 20-708 Lublin, PolandInstituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206 La Laguna, Tenerife, SpainDepartment of Molecular Biology, The John Paul II Catholic University of Lublin, ul. Konstantynów 1i, 20-708 Lublin, PolandInstituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez 2, 38206 La Laguna, Tenerife, SpainA new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 µg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes.http://www.mdpi.com/1420-3049/23/1/199triazolescoumarinantibacterial activityEnterococcus faecalisbiofilm |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Priscila López-Rojas Monika Janeczko Konrad Kubiński Ángel Amesty Maciej Masłyk Ana Estévez-Braun |
| spellingShingle |
Priscila López-Rojas Monika Janeczko Konrad Kubiński Ángel Amesty Maciej Masłyk Ana Estévez-Braun Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives Molecules triazoles coumarin antibacterial activity Enterococcus faecalis biofilm |
| author_facet |
Priscila López-Rojas Monika Janeczko Konrad Kubiński Ángel Amesty Maciej Masłyk Ana Estévez-Braun |
| author_sort |
Priscila López-Rojas |
| title |
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives |
| title_short |
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives |
| title_full |
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives |
| title_fullStr |
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives |
| title_full_unstemmed |
Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives |
| title_sort |
synthesis and antimicrobial activity of 4-substituted 1,2,3-triazole-coumarin derivatives |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2018-01-01 |
| description |
A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12.5–50 µg/mL). Moreover, the synthesized triazoles show relatively low toxicity against human erythrocytes. |
| topic |
triazoles coumarin antibacterial activity Enterococcus faecalis biofilm |
| url |
http://www.mdpi.com/1420-3049/23/1/199 |
| work_keys_str_mv |
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1725830083250225152 |