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Article

Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity

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Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland
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Associate Laboratory i4HB-Institute for Health and Bioeconomy, NOVA School of Science and Technology, NOVA University Lisbon, 2819-516 Caparica, Portugal
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UCIBIO—Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, NOVA University Lisbon, 2819-516 Caparica, Portugal
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Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland
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Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
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A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Ulitsa Vavilova 28, 119991 Moscow, Russia
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N.N Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ulitsa Kosygina 4, 119991 Moscow, Russia
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Chair of Chemistry and Physics, Plekhanov Russian University of Economics, Stremyannyi Pereulok 36, 117997 Moscow, Russia
*
Authors to whom correspondence should be addressed.
Academic Editor: Bartolo Gabriele
Molecules 2021, 26(21), 6364; https://doi.org/10.3390/molecules26216364
Received: 24 September 2021 / Revised: 15 October 2021 / Accepted: 18 October 2021 / Published: 21 October 2021
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)2-quin)2] (1), [VO(2,5-(Me)2-quin)2] (2) and [VO(2-Me-quin)2] (3). Complexes 13 demonstrated high catalytic activity in the oxidation of hydrocarbons with H2O2 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 1 and 2 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 3 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). View Full-Text
Keywords: vanadium(IV) complexes; biological activity; catalytic properties; 8-hydroxyquinoline; cytotoxicity studies vanadium(IV) complexes; biological activity; catalytic properties; 8-hydroxyquinoline; cytotoxicity studies
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MDPI and ACS Style

Palion-Gazda, J.; Luz, A.; Raposo, L.R.; Choroba, K.; Nycz, J.E.; Bieńko, A.; Lewińska, A.; Erfurt, K.; V. Baptista, P.; Machura, B.; Fernandes, A.R.; Shul’pina, L.S.; Ikonnikov, N.S.; Shul’pin, G.B. Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity. Molecules 2021, 26, 6364. https://doi.org/10.3390/molecules26216364

AMA Style

Palion-Gazda J, Luz A, Raposo LR, Choroba K, Nycz JE, Bieńko A, Lewińska A, Erfurt K, V. Baptista P, Machura B, Fernandes AR, Shul’pina LS, Ikonnikov NS, Shul’pin GB. Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity. Molecules. 2021; 26(21):6364. https://doi.org/10.3390/molecules26216364

Chicago/Turabian Style

Palion-Gazda, Joanna, 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, and Georgiy B. Shul’pin. 2021. "Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity" Molecules 26, no. 21: 6364. https://doi.org/10.3390/molecules26216364

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