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Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives.

European journal of medicinal chemistry (2011-06-18)
Juri M Timonen, Riina M Nieminen, Outi Sareila, Antonis Goulas, Lauri J Moilanen, Matti Haukka, Pirjo Vainiotalo, Eeva Moilanen, Paula H Aulaskari
RESUMEN

A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western blot, NO by nitrite assay and IL-6 by ELISA analyses. Fifteen of the tested 7-hydroxycoumarins also inhibited IL-6 production but none of them had any major inhibitory effect on COX-2 expression.

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Sigma-Aldrich
4-Methylumbelliferone, ≥98%
Sigma-Aldrich
Umbelliferone, 99%
Sigma-Aldrich
Umbelliferone, suitable for fluorescence indicator, ≥98.0% (HPLC)
Supelco
Umbelliferone, analytical standard