Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond(s) in the polyene spacer

European Journal of Medicinal Chemistry
D Hadjipavlou-LitinaDionissios Papaioannou

Abstract

Ester analogs of the antipsoriatic drug acitretin were synthesized by coupling either anilines with N-protected indole-3-carboxylic acid, followed by deprotection and coupling with O-monoprotected dicarboxylic acids or Wittig reaction of indole-3-carboxaldehyde, 3-acetyl-1-tosylpyrrole and 4-amino-9-fluorenone with Ph3P=CHCO2tBu, followed by N-deprotection, where necessary, and finally coupling with cinnamoyl fluorides. Corresponding free acids were obtained through TFA-mediated carboxyl group deprotection. Although these analogs and acitretin showed very low reducing abilities, analogs 5, 6, 8 and 12 strongly inhibited LOX with IC50 values ranging from 35-65 microM. Acitretin and its analogs 5-7, 10, 11 and 15 inhibited lipid peroxidation more strongly than trolox whereas acitretin and analog 4 were in vivo more potent anti-inflammatory agents on rat paw oedema induced by Carrageenan than indomethacin.

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Citations

Jan 8, 2013·European Journal of Medicinal Chemistry·Stavros E BariamisDimitra Hadjipavlou-Litina
Apr 22, 2011·Bioorganic & Medicinal Chemistry·Panagiota Moutevelis-MinakakisDimitra Hadjipavlou-Litina
Nov 3, 2010·Bioorganic & Medicinal Chemistry·Dimitra Hadjipavlou-LitinaDionissios Papaioannou
Apr 2, 2013·Biochimie·Dimitra Hadjipavlou-LitinaDionissios Papaioannou

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