Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
The direct acylation of quercetin ( I ) with 3-chloro-2,2-dimethylpropanoyl chloride ( II ) gives a complex reaction mixture. The synthesis of different acylated quercetin with from mono- to tetra-O-substituted functions was achieved in a simple procedure wherein the yield of isomers depended on the...
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Veröffentlicht in: | Chemical papers 2013, Vol.67 (1), p.76-83 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The direct acylation of quercetin (
I
) with 3-chloro-2,2-dimethylpropanoyl chloride (
II
) gives a complex reaction mixture. The synthesis of different acylated quercetin with from mono- to tetra-O-substituted functions was achieved in a simple procedure wherein the yield of isomers depended on the stoichiometric ratio of reagents. The crude reaction mixtures were analysed (LC-MS) and compared with the isolated products. Unambiguous structural characterisation of isomeric quercetin derivatives was confirmed by NMR analysis. In addition, the quercetin dimer can be obtained in a high yield in the simple procedure. The anti-oxidant activity and aldose reductase inhibition of the compounds were screened with the aim of providing bi-functional remedies to treat diabetic complications and other diseases where oxidative stress and the polyol pathway are key etiological factors. |
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ISSN: | 0366-6352 1336-9075 1336-9075 |
DOI: | 10.2478/s11696-012-0240-5 |