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

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Abstract

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.

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Acknowledgements

The authors would like to thank Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (Proc. 2014/07493-5), for their financial support and Coordenacão de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) for scholarship.

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Authors and Affiliations

  1. Department of Physical and Chemistry, Universidade Estadual Paulista Júlio de Mesquista Filho (UNESP), Ilha Solteria, São Paulo, Brazil

    Rosangela S. Laurentiz, Willian P. Gomes, Ana P. R. Pissurno & Fernanda A. Santos

  2. Research Laboratory in Applied Microbiology, Universidade de Franca, Franca, São Paulo, Brazil

    Vinicius Cristian O. Santos & Carlos H. G. Martins

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  1. Rosangela S. Laurentiz
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  2. Willian P. Gomes
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  3. Ana P. R. Pissurno
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  4. Fernanda A. Santos
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  5. Vinicius Cristian O. Santos
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  6. Carlos H. G. Martins
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Correspondence to Rosangela S. Laurentiz.

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Laurentiz, R.S., Gomes, W.P., Pissurno, A.P.R. et al. Synthesis and antibacterial activity of new lactone 1,4-dihydroquinoline derivatives. Med Chem Res 27, 1074–1084 (2018). https://doi.org/10.1007/s00044-017-2129-x

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  • DOI: https://doi.org/10.1007/s00044-017-2129-x

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