Citation:

Vanadium(IV) complexes with methyl-substituted 8-hydroxyquinolines: Catalytic potential in the oxidation of hydrocarbons and alcohols with peroxides and biological activity, Palion-Gazda, Joanna, Luz André, Raposo {Luis R. }, Choroba Katarzyna, Nycz {Jacek E. }, Bieńko Alina, Lewińska Agnieszka, Erfurt Karol, Baptista {Pedro V. }, Machura Barbara, Fernandes {Alexandra R. }, Shul’pina {Lidia S. }, Ikonnikov {Nikolay S. }, and Shul’pin {Georgiy B. } , Molecules, oct, Volume 26, Number 21, (2021)

Abstract:

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 1–3 demonstrated high catalytic activity in the oxidation of hydrocarbons with H2 O2 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 regioand 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).

Notes:

info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04378%2F2020/PT# info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04378%2F2020/PT# Nos. 19-03-00142 RFMEFI61917X0007 State Task 0082-2014-0007 (CITIS): AAAA-A17-117040610283-3 LA/P/0140/2020