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

Hélio A Stefani; Giancarlo V Botteselle; Julio Zukerman-Schpector; Ignez Caracelli; Denis da Silva Corrêa; Sandra H P Farsky; Isabel D Machado; José R Santin; Cristina B Hebeda

doi:10.1016/j.ejmech.2011.10.018

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

Eur J Med Chem. 2012 Jan;47(1):52-8. doi: 10.1016/j.ejmech.2011.10.018. Epub 2011 Oct 20.

Authors

Hélio A Stefani¹, Giancarlo V Botteselle, Julio Zukerman-Schpector, Ignez Caracelli, Denis da Silva Corrêa, Sandra H P Farsky, Isabel D Machado, José R Santin, Cristina B Hebeda

Affiliation

¹ Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil. hstefani@usp.br

PMID: 22071254
DOI: 10.1016/j.ejmech.2011.10.018

Abstract

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 PGE(2) secretion by LPS-stimulated neutrophils, suggesting selectivity for COX-2. Molecular docking studies in the binding site of COX-2 were performed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / chemistry
Amino Acids / metabolism
Amino Acids / pharmacology*
Anti-Inflammatory Agents / chemical synthesis*
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / metabolism
Anti-Inflammatory Agents / pharmacology*
Catalytic Domain
Cyclooxygenase 1 / chemistry
Cyclooxygenase 1 / metabolism
Cyclooxygenase 2 / chemistry
Cyclooxygenase 2 / metabolism
Cyclooxygenase 2 Inhibitors / chemical synthesis*
Cyclooxygenase 2 Inhibitors / chemistry
Cyclooxygenase 2 Inhibitors / metabolism
Cyclooxygenase 2 Inhibitors / pharmacology*
Models, Molecular*

Substances

Amino Acids
Anti-Inflammatory Agents
Cyclooxygenase 2 Inhibitors
Cyclooxygenase 1
Cyclooxygenase 2