7‐(2‐Oxoalkoxy)coumarins: Synthesis and Anti‐Inflammatory Activity of a Series of Substituted Coumarins |
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| Authors: | Juri Timonen Katriina Vuolteenaho Tiina Leppänen Riina Nieminen Eeva Moilanen Paula Aulaskari Janne Jänis |
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| Institution: | 1. Department of Chemistry, University of Eastern Finland, Joensuu, Finland;2. University of Tampere, School of Medicine, Tampere University, Hospital, Tampere, Finland |
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| Abstract: | A series of 7‐(2‐oxoalkoxy)coumarins have been synthesized by conjugating substituted 7‐hydroxycoumarins with different chloroketones. The anti‐inflammatory properties of 7‐(2‐oxoalkoxy)coumarins were studied in LPS‐induced inflammatory response in J774 macrophages. Western blot was used to determine the expression of iNOS and COX‐2, NO was determined by measuring its metabolite nitrite by Griess reaction and IL‐6 was measured by ELISA. Seventeen of the studied compounds inhibited NO and IL‐6 production over 50% at 100 μM concentrations. IC50 values of the best inhibitors were 21 μM/24 μM (NO/IL‐6) for compound 12 and 30 μM/10 μM (NO/IL‐6) for compound 20 . The main result was that the substitution with 7‐(2‐oxoalkoxy) group improved the anti‐inflammatory properties of most of the investigated 7‐hydroxycoumarins. |
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