Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity
Quinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against <i>E. coli</i> to a library of 1000 qu...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-07-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/15/7/818 |
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| author | Beatriz Suay-García Jose-Ignacio Bueso-Bordils Gerardo Antón-Fos María-Teresa Pérez-Gracia Antonio Falcó Pedro Alemán-López |
| author_facet | Beatriz Suay-García Jose-Ignacio Bueso-Bordils Gerardo Antón-Fos María-Teresa Pérez-Gracia Antonio Falcó Pedro Alemán-López |
| author_sort | Beatriz Suay-García |
| collection | DOAJ |
| description | Quinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against <i>E. coli</i> to a library of 1000 quinolones, two quinolones were selected to be synthesized. Additionally, a series of zwitterionic quinolonates were also synthesized. Quinolones and zwitterionic quinolonates were obtained by coupling the corresponding amine with reagent <b>1</b> in acetonitrile. Antibacterial activity was assessed using a microdilution method. All the compounds presented antibacterial activity, especially quinolones <b>2</b> and <b>3</b>, selected by the prediction model, which had broad-spectrum activity. Furthermore, a new type of zwitterionic quinolonate with antibacterial activity was found. These compounds can lead to a new line of antimicrobials, as the structures, and, therefore, their properties, are easily adjustable in the amine in position 4 of the pyridine ring. |
| first_indexed | 2024-03-09T10:13:14Z |
| format | Article |
| id | doaj.art-3b20a8659bc5402093a957d9801c6eb7 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-09T10:13:14Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-3b20a8659bc5402093a957d9801c6eb72023-12-01T22:33:20ZengMDPI AGPharmaceuticals1424-82472022-07-0115781810.3390/ph15070818Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic ActivityBeatriz Suay-García0Jose-Ignacio Bueso-Bordils1Gerardo Antón-Fos2María-Teresa Pérez-Gracia3Antonio Falcó4Pedro Alemán-López5ESI International Chair@CEU-UCH, Departamento de Matemáticas, Física y Ciencias Tecnológicas, Universidad Cardenal Herrera-CEU, CEU Universities San Bartolomé 55, 46115 Alfara del Patriarca, Valencia, SpainDepartamento de Farmacia, Universidad Cardenal Herrera-CEU, CEU Universities C/Ramón y Cajal s/n, 46115 Alfara del Patriarca, Valencia, SpainDepartamento de Farmacia, Universidad Cardenal Herrera-CEU, CEU Universities C/Ramón y Cajal s/n, 46115 Alfara del Patriarca, Valencia, SpainDepartamento de Farmacia, Universidad Cardenal Herrera-CEU, CEU Universities C/Ramón y Cajal s/n, 46115 Alfara del Patriarca, Valencia, SpainESI International Chair@CEU-UCH, Departamento de Matemáticas, Física y Ciencias Tecnológicas, Universidad Cardenal Herrera-CEU, CEU Universities San Bartolomé 55, 46115 Alfara del Patriarca, Valencia, SpainDepartamento de Farmacia, Universidad Cardenal Herrera-CEU, CEU Universities C/Ramón y Cajal s/n, 46115 Alfara del Patriarca, Valencia, SpainQuinolones are one of the most extensively used therapeutic families of antibiotics. However, the increase in antibiotic-resistant bacteria has rendered many of the available compounds useless. After applying our prediction model of activity against <i>E. coli</i> to a library of 1000 quinolones, two quinolones were selected to be synthesized. Additionally, a series of zwitterionic quinolonates were also synthesized. Quinolones and zwitterionic quinolonates were obtained by coupling the corresponding amine with reagent <b>1</b> in acetonitrile. Antibacterial activity was assessed using a microdilution method. All the compounds presented antibacterial activity, especially quinolones <b>2</b> and <b>3</b>, selected by the prediction model, which had broad-spectrum activity. Furthermore, a new type of zwitterionic quinolonate with antibacterial activity was found. These compounds can lead to a new line of antimicrobials, as the structures, and, therefore, their properties, are easily adjustable in the amine in position 4 of the pyridine ring.https://www.mdpi.com/1424-8247/15/7/818quinoloneantibioticantibiotic-resistant bacteriazwitterionic compounds |
| spellingShingle | Beatriz Suay-García Jose-Ignacio Bueso-Bordils Gerardo Antón-Fos María-Teresa Pérez-Gracia Antonio Falcó Pedro Alemán-López Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity Pharmaceuticals quinolone antibiotic antibiotic-resistant bacteria zwitterionic compounds |
| title | Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity |
| title_full | Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity |
| title_fullStr | Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity |
| title_full_unstemmed | Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity |
| title_short | Synthesis of Quinolones and Zwitterionic Quinolonate Derivatives with Broad-Spectrum Antibiotic Activity |
| title_sort | synthesis of quinolones and zwitterionic quinolonate derivatives with broad spectrum antibiotic activity |
| topic | quinolone antibiotic antibiotic-resistant bacteria zwitterionic compounds |
| url | https://www.mdpi.com/1424-8247/15/7/818 |
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