Treatment of acute and chronic inflammation still remains a challenge despite of the availability of numerous steroidal and non-steroidal drugs. All present medications, although very potent in alleviating the pain, fever, and swelling, exhibit serious side effects, such as stomach ulcers, kidney damage, and in some cases hearth attack and stroke. These possible complications limit the applications of most drugs and show the need for development of novel, less toxic agents. Flavonoids are a large group of compounds found in vascular plants and known for their broad range of biological activity. Some of them, such as cardamonin, are subject of extensive studies and clinical trials. The existing data about structure-activity relationship allow us to design novel, potentially more efficient synthetic derivatives. This research presents the synthesis and anti-inflammatory studies of substituted chalcones and Δ1-pyrroline-5-carbonitriles. Two of the compounds containing halogen substituents in ring “B” exhibit NO inhibition comparable to these of cardamonin and L-NIL used as standards, together with low (LC50 &gt; 65 mM) cytotoxicity. This activity disappears when the double bond is replaced with a pyrroline ring making the compounds more rigid. Overall, the substitution pattern in ring “B” together with the flexibility of the compound, are important for the anti-inflammatory efficiency. Further studies are in progress to clarify details about the mechanism of action of the most potent compounds.

Anti-inflammatory properties of synthetic chalcones and Δ1-pyrroline-5-carbonitriles

255th National Meeting (2018)

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