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钒(IV)配合物与甲基取代的 8-羟基喹啉：在过氧化物氧化烃和醇中的催化潜力和生物活性。

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

机构信息

Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland.

Associate Laboratory i4HB-Institute for Health and Bioeconomy, NOVA School of Science and Technology, NOVA University Lisbon, 2819-516 Caparica, Portugal.

出版信息

Molecules. 2021 Oct 21;26(21):6364. doi: 10.3390/molecules26216364.

DOI:10.3390/molecules26216364
PMID:34770772
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8588223/
Abstract

Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)-quin)] (), [VO(2,5-(Me)-quin)] () and [VO(2-Me-quin)] (). Complexes - demonstrated high catalytic activity in the oxidation of hydrocarbons with HO 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 and 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 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).

摘要

甲基取代的 8-羟基喹啉（Hquin）成功地用于合成五配位的氧化钒（IV）配合物：[VO(2,6-(Me)-quin)] ()、[VO(2,5-(Me)-quin)] ()和[VO(2-Me-quin)] ()。在 50°C 下，在乙腈中用 HO 氧化烃类时，配合物 - 表现出高催化活性，在 2-吡嗪羧酸（PCA）作为共催化剂存在的情况下。达到的环己烷氧化产物的最高产率为 48%，这在饱和烃的氧化中是很高的。反应导致环己基过氧化物、环己醇和环己酮的混合物的形成。当添加三苯基膦时，环己基过氧化物完全转化为环己醇。考虑到正庚烷和甲基环己烷分别的区域和键选择性氧化，表明氧化是在游离羟基自由基的参与下进行的。这些配合物在醇的氧化中表现出中等活性。配合物 和 降低结肠直肠（HCT116）和卵巢（A2780）癌细胞系的活力，并且对正常皮肤成纤维细胞没有表现出对癌细胞系的特异性选择性。另一方面，配合物 在结肠直肠癌细胞系（HCT116）中表现出更高的细胞毒性，对正常皮肤成纤维细胞的细胞毒性较低，对卵巢癌细胞系（HCT116 > 成纤维细胞 > A2780）没有影响。

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