Synthesis of Symmetrically Substituted 3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as Novel Quinoline Derivatives with Antibacterial Activity
| Autor: | Alexandre T. Neto, Teodoro S. Kaufman, Matías D. Ferretti, Enrique L. Larghi, Ademir F. Morel |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Stereochemistry
Microbial Sensitivity Tests Quinolones Gram-Positive Bacteria Ring (chemistry) Bioactive compounds Structure-Activity Relationship Broad spectrum chemistry.chemical_compound Minimum inhibitory concentration Gram-Negative Bacteria Drug Discovery Novel antibacterial heterocycles Pharmacology Dose-Response Relationship Drug Molecular Structure Organic Chemistry Quinoline Ciencias Químicas Aromaticity General Medicine Anti-Bacterial Agents Química Orgánica Nitrogen atom chemistry Mic values Quinolines 3 3-Dibenzyl-4-hydroxy-3 4-dihydro-1H-quinolin-2-ones Antibacterial activity CIENCIAS NATURALES Y EXACTAS |
| Popis: | A novel series of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones was synthesized and tested as antimicrobials. The minimum inhibitory concentration (MIC) values of the most active heterocycles were slightly higher than those exhibited by levofloxacin, employed as comparator. Structural factors affecting the activity were explored along three diversification points, including the substituents of the aromatic rings of the 3-benzyl moieties, as well as the functionalization of both, the homocyclic ring of the heterocycle and the quinolonic nitrogen atom. 6-Chloro and 3,3-bis(4′-chlorobenzyl) derivatives showed the lower MIC values. Optimally substituted heterocycles were synthesized, which exhibited enhanced activity. Fil: Ferretti, Matías D.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina Fil: Neto, Alexandre T.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil Fil: Morel, Ademir F.. Universidade Federal de Santa María. Núcleo de Pesquisas em Produtos Naturais; Brasil Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina Fil: Larghi, Enrique Leandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina |
| Databáze: | OpenAIRE |
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