Synthesis and antibacterial activity of new lactone 1,4-dihydroquinoline derivatives

In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized and characterized by 1H and 13C NMR. The synthesized compounds were evaluated for their in vitro antibacterial activity against the bacterial strains Porphyromonas gingivalis, Prevotella nigrescens, Str...

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Detalles Bibliográficos
Autores: Laurentiz, Rosangela S. [UNESP], Gomes, Willian P. [UNESP], Pissurno, Ana P. R. [UNESP], Santos, Fernanda A. [UNESP], Santos, Vinicius Cristian O., Martins, Carlos H. G.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:Brasil
Institución:Universidade Estadual Paulista (UNESP)
Repositorio:Repositório Institucional da UNESP
Idioma:inglés
OAI Identifier:oai:repositorio.unesp.br:11449/176043
Acceso en línea:http://dx.doi.org/10.1007/s00044-017-2129-x
http://hdl.handle.net/11449/176043
Access Level:acceso abierto
Palabra clave:antibacterial activity
Azo-heterocyclic compounds
quinoline derivatives
Descripción
Sumario:In this work, a series of lactone 1,4-dihydroquinoline derivatives 4 were efficiently synthesized and characterized by 1H and 13C NMR. The synthesized compounds were evaluated for their in vitro antibacterial activity against the bacterial strains Porphyromonas gingivalis, Prevotella nigrescens, Streptococcus mitis, and Streptococcus sanguinis and against Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The results revealed that the evaluated compounds were more active against Gram negative bacteria. Compounds 4ba, 4bb, 4bg, 4bi, 4bn, 4ch, and 4ci displayed moderate antibacterial activity against P. gingivalis. 4bi was the most active compound against the three strains of Mycobacterium. Based on structure–activity relationship studies, we observed that the presence of a nitro group on the benzylic ring and a methylenedioxy group on the dihydroquinoline ring enhanced the antibacterial activity of the derivatives.