Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives
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 (<b>3a</b>), chloro (<b>3b</b>), or bis-fluoro (<b>3d</b>) substitution on the biological activity of...
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MDPI AG
2023-10-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/20/15119 |
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| author | Andrei V. Bogdanov Margarita Neganova Alexandra Voloshina Anna Lyubina Syumbelya Amerhanova Igor A. Litvinov Olga Tsivileva Nurgali Akylbekov Rakhmetulla Zhapparbergenov Zulfiia Valiullina Alexandr V. Samorodov Igor Alabugin |
| author_facet | Andrei V. Bogdanov Margarita Neganova Alexandra Voloshina Anna Lyubina Syumbelya Amerhanova Igor A. Litvinov Olga Tsivileva Nurgali Akylbekov Rakhmetulla Zhapparbergenov Zulfiia Valiullina Alexandr V. Samorodov Igor Alabugin |
| author_sort | Andrei V. Bogdanov |
| collection | DOAJ |
| description | 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 (<b>3a</b>), chloro (<b>3b</b>), or bis-fluoro (<b>3d</b>) 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 <b>3a</b> and <b>3b</b> 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 <b>7c</b> and <b>5c</b>,<b>e</b> exhibit the highest antagonistic effect against phytopathogens of bacterial and fungal origin and can be considered useful leads for combating plant diseases. |
| first_indexed | 2024-03-10T21:13:16Z |
| format | Article |
| id | doaj.art-f1890d8445e543d0a8d83a9907f17f6f |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T21:13:16Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-f1890d8445e543d0a8d83a9907f17f6f2023-11-19T16:41:54ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-10-0124201511910.3390/ijms242015119Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone DerivativesAndrei V. Bogdanov0Margarita Neganova1Alexandra Voloshina2Anna Lyubina3Syumbelya Amerhanova4Igor A. Litvinov5Olga Tsivileva6Nurgali Akylbekov7Rakhmetulla Zhapparbergenov8Zulfiia Valiullina9Alexandr V. Samorodov10Igor Alabugin11Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaInstitute of Biochemistry and Physiology of Plants and Microorganisms, Saratov Scientific Centre of the Russian Academy of Sciences, Entuziastov Ave. 13, Saratov 410049, RussiaLaboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda 120014, KazakhstanLaboratory of Engineering Profile “Physical and Chemical Methods of Analysis”, Korkyt Ata Kyzylorda University, Aitekebie Str. 29A, Kyzylorda 120014, KazakhstanDepartment of Pharmacology, Bashkir State Medical University, Lenin St. 8, Ufa 450008, RussiaDepartment of Pharmacology, Bashkir State Medical University, Lenin St. 8, Ufa 450008, RussiaArbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov St. 8, Kazan 420088, RussiaA 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 (<b>3a</b>), chloro (<b>3b</b>), or bis-fluoro (<b>3d</b>) 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 <b>3a</b> and <b>3b</b> 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 <b>7c</b> and <b>5c</b>,<b>e</b> exhibit the highest antagonistic effect against phytopathogens of bacterial and fungal origin and can be considered useful leads for combating plant diseases.https://www.mdpi.com/1422-0067/24/20/15119isatinquaternary ammonium compoundscancerhydrazonescrystal structureantiphytopathogenes |
| spellingShingle | Andrei V. Bogdanov Margarita Neganova Alexandra Voloshina Anna Lyubina Syumbelya Amerhanova Igor A. Litvinov Olga Tsivileva Nurgali Akylbekov Rakhmetulla Zhapparbergenov Zulfiia Valiullina Alexandr V. Samorodov Igor Alabugin Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives International Journal of Molecular Sciences isatin quaternary ammonium compounds cancer hydrazones crystal structure antiphytopathogenes |
| title | Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives |
| title_full | Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives |
| title_fullStr | Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives |
| title_full_unstemmed | Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives |
| title_short | Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives |
| title_sort | anticancer and antiphytopathogenic activity of fluorinated isatins and their water soluble hydrazone derivatives |
| topic | isatin quaternary ammonium compounds cancer hydrazones crystal structure antiphytopathogenes |
| url | https://www.mdpi.com/1422-0067/24/20/15119 |
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