A Simple Procedure for Synthesis of Biological Active 4-oxo-4-(quinolin-8-yloxy)but-2-enoic acid
DOI:
https://doi.org/10.18321/ectj1148Keywords:
oxyquinoline, maleic anhydride, antimicrobial agents, NMR spectroscopyAbstract
The article is devoted to research on the synthesis of hydroxyquinoline derivative based on 8-oxyquinoline and maleic anhydride. Analysis of available literature was carried out, some drugs were found that are produced based on hydroxyquinoline derivatives and have antiprotozoal, antimicrobial and antiseptic effects, used alone or in combination with other active substances. A technique has been developed for the synthesis of a new derivative in the medium of petroleum distillate using sulfuric acid as a catalyst. A water-soluble ester of 8-oxyquinoline and maleic acid was obtained in good yield (95%), the structure of which was established based on UV, IR and NMR spectroscopy. By analogy with other oxyquinoline derivatives and the results of prediction bioactivity in the PASS program, the obtained derivative may be characterized by antifungal (antiseborrheic) action. It was determined its antibacterial properties at a concentration of 20.0–10.0 mg/cm3 as well as a significant antioxidant activity which is a useful biological property to expand the range of its application.
References
(1). Chemical Encyclopedia: in 5 volumes: v. 3: Copper - Polymeric. Ed.: Knunyants I.L. et. al. M.: Great Russian Encyclopedia, 1992, 639 p. ISBN 5-85270-039-8 (in Russian).
(2). V.A. Montes, R. Pohl, J. Shinar, P. Anzenbacher, Chem. Eur. J. 12 (2006) 4523‒4535. Crossref
(3). Small Medical Encyclopedia. Ed. V.I. Pokrovsky, M., “Medicine”, V. 4. Nephrotomy ‒ Kidney failure. 1996, 576 p. ISBN 5-225- 02819-5 (in Russian).
(4). I.N. Gaisina, A.Yu. Khristichenko, A.M. Gaisin, N.A. Smirnova, I.G. Gazaryan, A.A. Poloznikov, Russ. Chem. Bull. 67 (2018) 2320–2322. Crossref
(5). M. Rbaa, A. Hichar, O. Bazdi, Y. Lakhrissi, K. Ounine, B. Lakhrissi, Beni-Suef. Univ. J. Basic Appl. Sci. 8 (2019). Crossref
(6). H.-G. Fu, Z.-W. Li, X.-X. Hu, S.-Y. Si, X.-F. You, S. Tang, Y.-X. Wang, D.-Q. Song, Molecules 24 (2019) 548. Crossref
(7). T.A. Chupakhina, A.M. Katsev, V.O. Kur’yanov, Russ. J. Bioorg. Chem. 38 (2012) 422–427. Crossref
(8). M. Ahmed, R. Sharma, D.P. Nagda, J.L. Jat, G.L. Talesara, ARKIVOC 11 (2006) 66–75. Crossref
(9). S.K. Kabieva, O.A. Nurkenov, T.M. Seilkhanov, A.A. Bakibaev, A.M. Gazaliev, A.T. Takibaeva, O.A. Voronova, E.V. Plotnikov, Russ. J. Gen. Chem. 86 (2016) 1765–1768. Crossref
(10). Patent RU2535140C1. Composition with antioxidant and antibacterial activity. Publ. 10.12.2014 (in Russian).
(11). Chemical Encyclopedia: in 5 volumes: v. 2: Daf-Med. Ed. Knunyants I.L. et al. M.: Soviet Encyclopedia, 1990, 671 p. ISBN 5-82270-035- 5 (in Russian).
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