6-Chloro-3-nitro-4-hydroxyquinolin-2(1H)-one as an efficient antibacterial agent
محورهای موضوعی : Biotechnological Journal of Environmental Microorganisms
1 - گروه شیمی، دانشکده علوم پایه ، واحد لاهیجان ، دانشگاه آزاد اسلامی، لاهیجان ایران
کلید واژه: 4-hydroxy quinolin-2(1H)-one, Nitration, Spectroscopy, Antibacterial activities,
چکیده مقاله :
In this study, 4-chloroaniline was first reacted with diethyl malonate to yield the corresponding malonodianilide.
Then, this compound was cyclized to 6-chloro-4-hydroxyquinolin-2(1H)-one in melted polyphosphoric
acid at 140-150°C. 6-Chloro-3-nitro-4-hydroxyquinolin-2(1H)-one was successfully synthesized from
6-chloro-4-hydroxyquinolin-2(1H)-one through a traditional nitration process. After workup and purification
process, this compound was characterized using Fourier transform infrared (FT-IR) and proton nuclear magnetic
resonance (1H NMR) spectroscopic techniques. The antibacterial activities of the nitration product dissolved
in DMSO were then evaluated using the well diffusion method against Staphylococcus aureus (ATCC
25923), Escherichia coli (ATCC 25922), Proteus vulgaris (ATCC 49132), and Listeria monocytogenes (ATCC
1298) bacterial strains.
In this study, 4-chloroaniline was first reacted with diethyl malonate to yield the corresponding malonodianilide.
Then, this compound was cyclized to 6-chloro-4-hydroxyquinolin-2(1H)-one in melted polyphosphoric
acid at 140-150°C. 6-Chloro-3-nitro-4-hydroxyquinolin-2(1H)-one was successfully synthesized from
6-chloro-4-hydroxyquinolin-2(1H)-one through a traditional nitration process. After workup and purification
process, this compound was characterized using Fourier transform infrared (FT-IR) and proton nuclear magnetic
resonance (1H NMR) spectroscopic techniques. The antibacterial activities of the nitration product dissolved
in DMSO were then evaluated using the well diffusion method against Staphylococcus aureus (ATCC
25923), Escherichia coli (ATCC 25922), Proteus vulgaris (ATCC 49132), and Listeria monocytogenes (ATCC
1298) bacterial strains.
F. O’Donnell, T.J.P. Smyth, V.N. Ramachandran, W.F. Smyth, a study of the antimicrobial activity of selected synthetic and naturally occurring quinolones. Int. J. Antimicrob. Agents 35 (2010) 30-38.
[2] M. M. Abdou, Chemistry of 4-Hydroxy-2(1H)-quinolone. Part 1: Synthesis and reactions Arabian Journal of Chemistry 10 (2017), S3324–S3337, http://dx.doi.org/10.1016/j.arabjc.2014.01.012.
[3] G.S. Bisacch, Origins of the quinolone class of antibacterials: an expanded “discovery story”. J. Med. Chem. 58 (2015) 4874–4882, https ://doi.org/10.1021/jm501 881c.
[4] J.P. Michael, Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 20 (2003) 476-493.
[5] A. A. Aly, E. M. El‑Sheref, A.‑F. E. Mourad, M. E. M. Bakheet, S. Bräse, 4‑Hydroxy‑2‑quinolones: syntheses, reactions and fused heterocycles. Molecular Diversity 24 (2020) 477-524, https://doi.org/10.1007/s11030-019-09952-5.
[6] M. D. Ferretti, A. T. Neto, A. F. Morel, T. S. Kaufman, E. L. Larghi, Synthesis of symmetrically substituted 3,3-dibenzyl-4-hydroxy-3,4- dihydro-1H-quinolin-2-ones, as novel quinoline derivatives with antibacterial activityEuropean Journal of Medicinal Chemistry 81 (2014) 253-266.
[7] V. Dolle, E. Fan, C. H. Nguyen, A.M. Aubertin, A. Kirn, M.L. Andreola, G. Jamieson, L.T. Litvak, E. Bisagni, Journal of Medicinal Chemistry 38 (1995) 4679-4686, https://doi.org/10.1021/jm00023a007.
[8] D. Audisio, S. Messaoudi, J.F. Peyrat, J.D. Brion, M. Alami, L. Cegielkowski, D. Methy-Gonnot, C. Radanyi, J. M. Renoir, Discovery and Biological Activity of 6BrCaQ as an Inhibitor of the Hsp90 Protein Folding Machinery. Chem Med Chem 6 (2011) 804-815, https://doi.org/10.1002/cmdc.201000489.
[9] S.X. Cai, Z.L. Zhou, J.C. Huang, E.R. Whittemore, Z.O. Egbuwoku, J.E. Egbuwoku, J.E. Hawkinson, R.M. Woodward, E. Weber, J.F.W. Keana, Structure−Activity Relationships of 4-Hydroxy-3-nitroquinolin-2(1H)-ones as Novel Antagonists at the Glycine Site of N-Methyl-d-aspartate Receptors. Journal of Medicinal Chemistry 39 (1996) 4682-4686, https://doi.org/10.1021/jm960520y.
[10] N.M. Shukla, S.S. Malladi, C.A. Mutz, R. Balakrishna, S.A. David, Structure−Activity Relationships in Human Toll-Like Receptor 7-Active Imidazoquinoline Analogues. Journal of Medicinal Chemistry 53(2010) 4450-4465, https://doi.org/10.1021/jm100358c.
[11] A. Oeveren, M. Motamedi, E. Martinborough, S. Zhao, Y. Shen, S. West, W. Chang, A. Kallel, K.B. Marschke, F.J. Lopez, A. Negro-Vilar, L. Zhi, Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones.Bioorganic & Medicinal Chemistry Letters 17 (2007) 1527-1531, https://doi.org/10.1016/j.bmcl.2007.01.001.
[12] D.R. Buckle, B.C.C. Cantello, H. Smith, B.A. Spicer, 4-Hydroxy-3-nitro-2-quinolones and related compounds as inhibitors of allergic reactions. Journal of Medicinal Chemistry 1975, 18(1975) 726–732, https://doi.org/10.1021/jm00241a01.
[13] https://www.biosynth.com/p/FH159597/15151-57-2-4-hydroxy-3-nitro-21h-quinolinone
