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Synthesis of New 2-Amino-6-(4-hydroxy-2-oxo-chromen-3-yl)-4-aryl Nicotine Nitrile in Eco-Friendly Media and their Antimicrobials and DPPH Radical Scavenging Activities
Corresponding Author(s) : Naceur Hamdi
Asian Journal of Chemistry,
Vol. 31 No. 7 (2019): Vol 31 Issue 7
Abstract
A simple, green, efficient and economical procedure for the synthesis of, 2-amino-6-(4-hydroxy-2-oxo-chromen-3-yl)-4-(aryl) nicotine nitrile (4a-g) by two routes carried in same conditions, have been reported. The new compounds 4a-g were characterized by 1H NMR, 13C NMR, FT-IR and elemental analysis. The synthesized compounds were screened for their antibacterial activities against Gram-positive bacterial strains (Micrococcus luteus LB14110, Staphylococcus aureus ATCC 6538, Listeria monocytogenes ATCC 19117), Gram-negative bacteria (Escherichia coli, Salmonella typhimurium ATCC 14028 and Pseudomonas aeruginosa). The coumarin derivative 4a and 3-acetyl-4-hydroxycouamrin (1) were the most active against two bacteria Staphylococcus aureus ATCC 6538 and Candida albicans respectively. The best minimum inhibitory concentration values were obtained for the compound 4a against Candida albicans (0.0195 g/cm3). In addition, compounds 4a-g were investigated for their antioxidant activities by DPPH (2,2-diphenyl-1-picrylhydrazyl) in which most of them displayed significant antioxidant activities.
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P. Borah, P. Seetham Naidu and P.J. Bhuyan, Tetrahedron Lett., 53, 5034 (2012); https://doi.org/10.1016/j.tetlet.2012.07.060.
S.L. El-Ansary, S.E. Abbas, A.N. Mikhael and H.A. El-Banna, Egypt. J. Pharm. Sci., 33, 639 (1992).
S. Manfredini, D. Simoni, R. Ferroni, R. Bazzanini, S. Vertuani, S. Hatse, J. Balzarini and E. De Clercq, J. Med. Chem., 40, 3851 (1997); https://doi.org/10.1021/jm9602322.
L.W. Wattenberg, K.T. Lam and A.V. Fladmoe, Cancer Res., 39, 1651 (1979).
Y. Kashman, K.R. Gustafson, R.W. Fuller, J.H. Cardellina, J.B. McMahon, M.J. Currens, R.W. Buckheit, S.H. Hughes, G.M. Cragg and M.R. Boyd, J. Med. Chem., 35, 2735 (1992); https://doi.org/10.1021/jm00093a004.
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N.F. Anjum, A. Aleem, N. Nayeem and S.M. Asdaq, Der Pharm. Chem., 3, 56 (2011).
S.M. De Souza, F. Delle Monache and A. Smânia Jr., Z. Naturforsch. C, 60, 693 (2005); https://doi.org/10.1515/znc-2005-9-1006.
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J. Jung, J. Kim and O. Park, Synth. Commun., 29, 3587 (1999); https://doi.org/10.1080/00397919908085993.
W.M. Barker, M.A. Hermodson and K.P. Link, J. Med. Chem., 14, 167 (1971); https://doi.org/10.1021/jm00284a022.
M. Greaves, PLoS Med., 2, 342 (2005); https://doi.org/10.1371/journal.pmed.0020342.
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R. de Araújo, F. Guerra, E. de O. Lima, C. de Simone, J. Tavares, L. Scotti, M. Scotti, T. de Aquino, R. de Moura, F. Mendonça and J. BarbosaFilho, Int. J. Mol. Sci., 14, 1293 (2013); https://doi.org/10.3390/ijms14011293.
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J. Raboin, M. Beley and G. Kirsch, Tetrahedron Lett., 41, 1175 (2000); https://doi.org/10.1016/S0040-4039(99)02255-8.
N.B. Karatzas, Hellenic J. Cardiol., 55, 89 (2014).
N. Touj, A. Chakchouk-Mtibaa, L. Mansour, A.H. Harrath, J.H. Al-Tamimi, I. Özdemir, L. Mellouli, S. Yasar and N. Hamdi, J. Organomet. Chem., 853, 49 (2017); https://doi.org/10.1016/j.jorganchem.2017.09.024.
K. Güven, E. Yücel and F. Cetintas, Pharm. Biol., 44, 79 (2006); https://doi.org/10.1080/13880200600591253.
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A.J. Kirby and R. Schmidt, J. Ethnopharmacol., 56, 103 (1997); https://doi.org/10.1016/S0378-8741(97)01510-9.
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P.P. Ghosh and A.R. Das, Tetrahedron Lett., 53, 3140 (2012); https://doi.org/10.1016/j.tetlet.2012.04.033.
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S. Khodabakhshi and B. Karami, Tetrahedron Lett., 55, 7136 (2014); https://doi.org/10.1016/j.tetlet.2014.11.016.
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J.C. Cappuccino and N. Sherman, Microbiology-A Laboratory Manual, Addison Wesley: California, USA, p. 263 (1999).