Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity
Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>1</b>), [VO(2,5-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>2&...
Guardado en:
| Autores principales: | , , , , , , , , , , , , , |
|---|---|
| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
MDPI AG
2021
|
| Materias: | |
| Acceso en línea: | https://doaj.org/article/b6ab091820e54c8099466e8c4ea002f2 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| id |
oai:doaj.org-article:b6ab091820e54c8099466e8c4ea002f2 |
|---|---|
| record_format |
dspace |
| spelling |
oai:doaj.org-article:b6ab091820e54c8099466e8c4ea002f22021-11-11T18:23:27ZVanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity10.3390/molecules262163641420-3049https://doaj.org/article/b6ab091820e54c8099466e8c4ea002f22021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6364https://doaj.org/toc/1420-3049Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>1</b>), [VO(2,5-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>2</b>) and [VO(2-Me-quin)<sub>2</sub>] (<b>3</b>). Complexes <b>1</b>–<b>3</b> demonstrated high catalytic activity in the oxidation of hydrocarbons with H<sub>2</sub>O<sub>2</sub> in acetonitrile at 50 °C, in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst. The maximum yield of cyclohexane oxidation products attained was 48%, which is high in the case of the oxidation of saturated hydrocarbons. The reaction leads to the formation of a mixture of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. When triphenylphosphine is added, cyclohexyl hydroperoxide is completely converted to cyclohexanol. Consideration of the regio- and bond-selectivity in the oxidation of n-heptane and methylcyclohexane, respectively, indicates that the oxidation proceeds with the participation of free hydroxyl radicals. The complexes show moderate activity in the oxidation of alcohols. Complexes <b>1</b> and <b>2</b> reduce the viability of colorectal (HCT116) and ovarian (A2780) carcinoma cell lines and of normal dermal fibroblasts without showing a specific selectivity for cancer cell lines. Complex <b>3</b> on the other hand, shows a higher cytotoxicity in a colorectal carcinoma cell line (HCT116), a lower cytotoxicity towards normal dermal fibroblasts and no effect in an ovarian carcinoma cell line (order of magnitude HCT116 > fibroblasts > A2780).Joanna Palion-GazdaAndré LuzLuis R. RaposoKatarzyna ChorobaJacek E. NyczAlina BieńkoAgnieszka LewińskaKarol ErfurtPedro V. BaptistaBarbara MachuraAlexandra R. FernandesLidia S. Shul’pinaNikolay S. IkonnikovGeorgiy B. Shul’pinMDPI AGarticlevanadium(IV) complexesbiological activitycatalytic properties8-hydroxyquinolinecytotoxicity studiesOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6364, p 6364 (2021) |
| institution |
DOAJ |
| collection |
DOAJ |
| language |
EN |
| topic |
vanadium(IV) complexes biological activity catalytic properties 8-hydroxyquinoline cytotoxicity studies Organic chemistry QD241-441 |
| spellingShingle |
vanadium(IV) complexes biological activity catalytic properties 8-hydroxyquinoline cytotoxicity studies Organic chemistry QD241-441 Joanna Palion-Gazda André Luz Luis R. Raposo Katarzyna Choroba Jacek E. Nycz Alina Bieńko Agnieszka Lewińska Karol Erfurt Pedro V. Baptista Barbara Machura Alexandra R. Fernandes Lidia S. Shul’pina Nikolay S. Ikonnikov Georgiy B. Shul’pin Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| description |
Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>1</b>), [VO(2,5-(Me)<sub>2</sub>-quin)<sub>2</sub>] (<b>2</b>) and [VO(2-Me-quin)<sub>2</sub>] (<b>3</b>). Complexes <b>1</b>–<b>3</b> demonstrated high catalytic activity in the oxidation of hydrocarbons with H<sub>2</sub>O<sub>2</sub> in acetonitrile at 50 °C, in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst. The maximum yield of cyclohexane oxidation products attained was 48%, which is high in the case of the oxidation of saturated hydrocarbons. The reaction leads to the formation of a mixture of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. When triphenylphosphine is added, cyclohexyl hydroperoxide is completely converted to cyclohexanol. Consideration of the regio- and bond-selectivity in the oxidation of n-heptane and methylcyclohexane, respectively, indicates that the oxidation proceeds with the participation of free hydroxyl radicals. The complexes show moderate activity in the oxidation of alcohols. Complexes <b>1</b> and <b>2</b> reduce the viability of colorectal (HCT116) and ovarian (A2780) carcinoma cell lines and of normal dermal fibroblasts without showing a specific selectivity for cancer cell lines. Complex <b>3</b> on the other hand, shows a higher cytotoxicity in a colorectal carcinoma cell line (HCT116), a lower cytotoxicity towards normal dermal fibroblasts and no effect in an ovarian carcinoma cell line (order of magnitude HCT116 > fibroblasts > A2780). |
| format |
article |
| author |
Joanna Palion-Gazda André Luz Luis R. Raposo Katarzyna Choroba Jacek E. Nycz Alina Bieńko Agnieszka Lewińska Karol Erfurt Pedro V. Baptista Barbara Machura Alexandra R. Fernandes Lidia S. Shul’pina Nikolay S. Ikonnikov Georgiy B. Shul’pin |
| author_facet |
Joanna Palion-Gazda André Luz Luis R. Raposo Katarzyna Choroba Jacek E. Nycz Alina Bieńko Agnieszka Lewińska Karol Erfurt Pedro V. Baptista Barbara Machura Alexandra R. Fernandes Lidia S. Shul’pina Nikolay S. Ikonnikov Georgiy B. Shul’pin |
| author_sort |
Joanna Palion-Gazda |
| title |
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| title_short |
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| title_full |
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| title_fullStr |
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| title_full_unstemmed |
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity |
| title_sort |
vanadium(iv) complexes with methyl-substituted 8-hydroxyquinolines: catalytic potential in the oxidation of hydrocarbons and alcohols with peroxides and biological activity |
| publisher |
MDPI AG |
| publishDate |
2021 |
| url |
https://doaj.org/article/b6ab091820e54c8099466e8c4ea002f2 |
| work_keys_str_mv |
AT joannapaliongazda vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT andreluz vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT luisrraposo vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT katarzynachoroba vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT jacekenycz vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT alinabienko vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT agnieszkalewinska vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT karolerfurt vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT pedrovbaptista vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT barbaramachura vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT alexandrarfernandes vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT lidiasshulpina vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT nikolaysikonnikov vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity AT georgiybshulpin vanadiumivcomplexeswithmethylsubstituted8hydroxyquinolinescatalyticpotentialintheoxidationofhydrocarbonsandalcoholswithperoxidesandbiologicalactivity |
| _version_ |
1718431845877547008 |