Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents
The previously reported as well as newly synthesized derivatives of the 1-oxa-9-azaspiro[5.5]undecane were employed in the synthesis of thirty-six derivatives of ciprofloxacin using commercially available 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and the literature...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/15/4864 |
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| author | Alexei Lukin Mikhail Chudinov Tatiana Vedekhina Elizaveta Rogacheva Lyudmila Kraeva Olga Bakulina Mikhail Krasavin |
| author_facet | Alexei Lukin Mikhail Chudinov Tatiana Vedekhina Elizaveta Rogacheva Lyudmila Kraeva Olga Bakulina Mikhail Krasavin |
| author_sort | Alexei Lukin |
| collection | DOAJ |
| description | The previously reported as well as newly synthesized derivatives of the 1-oxa-9-azaspiro[5.5]undecane were employed in the synthesis of thirty-six derivatives of ciprofloxacin using commercially available 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and the literature protocol involving the preparation of boron chelate complex to facilitate nucleophilic aromatic substitution. All new fluoroquinolone derivatives were tested against two gram-positive as well as three gram-negative strains of bacteria. With the activity spectrum of the new derivatives being substantially narrower than that of ciprofloxacin, compounds were distinctly active against two of the five strains: gram-negative <i>Acinetobacter baumannii</i> 987<sup>®</sup> and gram-positive <i>Bacillus cereus</i> 138<sup>®</sup>. Towards these two strains, a large group of compounds displayed equal or higher potency than ciprofloxacin. |
| first_indexed | 2024-03-09T05:10:07Z |
| format | Article |
| id | doaj.art-7104e93f92364046ae19f85c2d4ccfe3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:10:07Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7104e93f92364046ae19f85c2d4ccfe32023-12-03T12:50:10ZengMDPI AGMolecules1420-30492022-07-012715486410.3390/molecules27154864Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial AgentsAlexei Lukin0Mikhail Chudinov1Tatiana Vedekhina2Elizaveta Rogacheva3Lyudmila Kraeva4Olga Bakulina5Mikhail Krasavin6Lomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 119454 Moscow, RussiaLomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 119454 Moscow, RussiaFederal Research and Clinical Center of Physico-Chemical Medicine, 1a Malaya Pirogovskaya Street, 119435 Moscow, RussiaPasteur Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 Saint Petersburg, RussiaPasteur Institute of Epidemiology and Microbiology, 14 Mira Street, 197101 Saint Petersburg, RussiaSaint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, RussiaSaint Petersburg State University, 26 Universitetskii Prospect, 198504 Peterhof, RussiaThe previously reported as well as newly synthesized derivatives of the 1-oxa-9-azaspiro[5.5]undecane were employed in the synthesis of thirty-six derivatives of ciprofloxacin using commercially available 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and the literature protocol involving the preparation of boron chelate complex to facilitate nucleophilic aromatic substitution. All new fluoroquinolone derivatives were tested against two gram-positive as well as three gram-negative strains of bacteria. With the activity spectrum of the new derivatives being substantially narrower than that of ciprofloxacin, compounds were distinctly active against two of the five strains: gram-negative <i>Acinetobacter baumannii</i> 987<sup>®</sup> and gram-positive <i>Bacillus cereus</i> 138<sup>®</sup>. Towards these two strains, a large group of compounds displayed equal or higher potency than ciprofloxacin.https://www.mdpi.com/1420-3049/27/15/4864antibacterialciprofloxacinaromatic nucleophilic substitutionspirocyclicpiperidines |
| spellingShingle | Alexei Lukin Mikhail Chudinov Tatiana Vedekhina Elizaveta Rogacheva Lyudmila Kraeva Olga Bakulina Mikhail Krasavin Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents Molecules antibacterial ciprofloxacin aromatic nucleophilic substitution spirocyclic piperidines |
| title | Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents |
| title_full | Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents |
| title_fullStr | Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents |
| title_full_unstemmed | Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents |
| title_short | Exploration of Spirocyclic Derivatives of Ciprofloxacin as Antibacterial Agents |
| title_sort | exploration of spirocyclic derivatives of ciprofloxacin as antibacterial agents |
| topic | antibacterial ciprofloxacin aromatic nucleophilic substitution spirocyclic piperidines |
| url | https://www.mdpi.com/1420-3049/27/15/4864 |
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