Synthesis and structural elucidation of a series of isoflavones-based on FPR antagonists

Authors

• Eugenio Uriarte Department of Organic Chemistry, FFaculty of Pharmacy, Universidad of Santiago de Compostela, Santiago de Compostela,
• Fernanda Borges CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007, Porto, Portugal
• Alexandra Gaspar CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007, Porto, Portugal.

Abstract

Isoflavones are naturally occurring compounds well-known for their beneficial role in several diseases, such as cancer and inflammation. Recently some isoflavones derivatives were reported as potent and competitive antagonists of formyl peptide receptors (FPRs) with an important role in regulating the inflammatory process. As a result of their biological activities, there is a huge interest in developing synthetic procedures to obtain isoflavones. Surprisingly, and as far as our knowledge goes, the synthetic work and full characterisation of the isoflavones described as FPR antagonists weren’t yet reported. The work herein described comprises the synthesis of two series of 2-trifluoromethyl isoflavones, including the ones described as FPR antagonists and their complete characterisation by 1D, 2D NMR techniques and high-resolution mass spectroscopy.