Synthesis, anti-inflammatory activity and molecular docking studies of 2,5-diarylfuran amino acid derivatives

A series of 2,5-diaryl substituted furans functionalized with several amino acids were synthesized and evaluated as the cyclooxygenases COX-1 and COX-2 enzymes inhibitors. The proline-substituted compound inhibited PGE2 secretion by LPS-stimulated neutrophils, suggesting selectivity for COX-2. Molecular docking studies in the binding site of COX-2 were performed.

Describe herein the synthesis of a novel 2,5-diarylfuran scaffold suitable for conjugation with amino acids. We also show that the proline-substituted compound inhibited PGE2 secretion by LPS-stimulated neutrophils, suggesting selectivity for COX-2 activity. Molecular docking studies, in COX-2, were performed in order to shed light on the nature of their different activities. The biological and docking results showed that the activity of this kind of molecule can be modulated by the hydrophilicity of the conjugated amino acid.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of a novel 2,5-diarylfuran scaffold and its conjugation with amino acids.
► The compound with proline inhibited PGE2 secretion suggesting COX-2 selectivity.
► Docking studies were carried out.
► The activity can be modulated by the hydrophilicity of the conjugated amino acid.