Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives
Bogdanov A.V. Neganova M. Voloshina A. Lyubina A. Amerhanova S. Litvinov I.A. Tsivileva O. Akylbekov N. Zhapparbergenov R. Valiullina Z. Samorodov A.V. Alabugin I.
October 2023Multidisciplinary Digital Publishing Institute (MDPI)
International Journal of Molecular Sciences
2023#24Issue 20
A series of new fluorinated 1-benzylisatins was synthesized in high yields via a simple one-pot procedure in order to explore the possible effect of ortho-fluoro (3a), chloro (3b), or bis-fluoro (3d) substitution on the biological activity of this pharmacophore. Furthermore, the new isatins could be converted into water-soluble isatin-3-hydrazones using their acid-catalyzed reaction with Girard’s reagent P and its dimethyl analog. The cytotoxic action of these substances is associated with the induction of apoptosis caused by mitochondrial membrane dissipation and stimulated reactive oxygen species production in tumor cells. In addition, compounds 3a and 3b exhibit platelet antiaggregation activity at the level of acetylsalicylic acid, and the whole series of fluorine-containing isatins does not adversely affect the hemostasis system as a whole. Among the new water-soluble pyridinium isatin-3-acylhydrazones, compounds 7c and 5c,e exhibit the highest antagonistic effect against phytopathogens of bacterial and fungal origin and can be considered useful leads for combating plant diseases.
antiphytopathogenes , cancer , crystal structure , cytotoxicity , hydrazones , isatin , quaternary ammonium compounds
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Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan, 420088, Russian Federation
Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Severnij Pr. 1, Chernogolovka, 142432, Russian Federation
Institute of Biochemistry and Physiology of Plants and Microorganisms, Saratov Scientific Centre of the Russian Academy of Sciences, Entuziastov Ave. 13, Saratov, 410049, Russian Federation
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda, 120014, Kazakhstan
Department of Pharmacology, Bashkir State Medical University, Lenin St. 8, Ufa, 450008, Russian Federation
Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, 32306-4390, FL, United States
Arbuzov Institute of Organic and Physical Chemistry
Institute of Physiologically Active Compounds
Institute of Biochemistry and Physiology of Plants and Microorganisms
Laboratory of Engineering Profile “Physical and Chemical Methods of Analysis”
Department of Pharmacology
Department of Chemistry and Biochemistry
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