A Simple Procedure for Synthesis of Biological Active 4-oxo-4-(quinolin-8-yloxy)but-2-enoic acid

V.V. Merkulov; A.I. Almazov; S.K. Kabiyeva; S.N. Mantler; V.V. Konshin

doi:10.18321/ectj1148

Authors

V.V. Merkulov Karaganda Industrial University, 30, Republic Ave., Temirtau, Kazakhstan
A.I. Almazov Karaganda Industrial University, 30, Republic Ave., Temirtau, Kazakhstan
S.K. Kabiyeva Karaganda Industrial University, 30, Republic Ave., Temirtau, Kazakhstan
S.N. Mantler Karaganda Industrial University, 30, Republic Ave., Temirtau, Kazakhstan
V.V. Konshin Polzunov Altai State Technical University, 46, Lenin Ave., Barnaul, Russian Federation

DOI:

https://doi.org/10.18321/ectj1148

Keywords:

oxyquinoline, maleic anhydride, antimicrobial agents, NMR spectroscopy

Abstract

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.

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