Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activity.
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.
Instituto de Química Rosario (CONICET-UNR), Suipacha 531, Rosario S2002LRK, Argentina.
Matías D
MD
Ferretti
Núcleo de Pesquisas em Produtos Naturais, Prédio 18, Universidade Federal de Santa María, Santa Maria, RS, Brazil.
Alexandre T
AT
Neto
Núcleo de Pesquisas em Produtos Naturais, Prédio 18, Universidade Federal de Santa María, Santa Maria, RS, Brazil. Electronic address: afmorel@base.ufsm.br.
Ademir F
AF
Morel
Instituto de Química Rosario (CONICET-UNR), Suipacha 531, Rosario S2002LRK, Argentina.
Teodoro S
TS
Kaufman
Instituto de Química Rosario (CONICET-UNR), Suipacha 531, Rosario S2002LRK, Argentina. Electronic address: larghi@iquir-conicet.gov.ar.
Enrique L
EL
Larghi
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000166:cytology / Q000187:drug effects / Q000254:growth & development; D006094:Gram-Positive Bacteria / Q000166:cytology / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D011804:Quinolines; D015363:Quinolones; C037219:quinoline
3,3-Dibenzyl-4-hydroxy-3,4-dihydro-1H-quinolin-2-ones; Bioactive compounds; Broad spectrum; Novel antibacterial heterocycles