Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters

Jérémie Doiron; Luc H Boudreau; Nadia Picot; Benoît Villebonet; Marc E Surette; Mohamed Touaibia

doi:10.1016/j.bmcl.2008.12.108

Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoyl clusters

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1118-21. doi: 10.1016/j.bmcl.2008.12.108. Epub 2009 Jan 3.

Authors

Jérémie Doiron¹, Luc H Boudreau, Nadia Picot, Benoît Villebonet, Marc E Surette, Mohamed Touaibia

Affiliation

¹ Department of Chemistry and Biochemistry, Université de Moncton, Moncton, NB, Canada E1A 3E9.

PMID: 19152786
DOI: 10.1016/j.bmcl.2008.12.108

Abstract

Novel cinnamoyl and caffeoyl clusters were synthesized by multiple Cu(I)-catalyzed [1,3]-dipolar cycloadditions and their anti-5-lipoxygenase inhibitory activity was tested. Caffeoyl cluster showed an improved 5-lipoxygenase inhibitory activity compared to caffeic acid, with caffeoyl trimer 16 and tetramer 19 showing the best 5-lipoxygenase inhibitory activity.

Publication types

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

MeSH terms

Caffeic Acids / chemical synthesis*
Caffeic Acids / chemistry
Caffeic Acids / pharmacology
Cinnamates / chemical synthesis*
Cinnamates / chemistry
Cinnamates / pharmacology
Combinatorial Chemistry Techniques
Drug Design
Lipoxygenase Inhibitors* / chemical synthesis*
Lipoxygenase Inhibitors* / chemistry
Lipoxygenase Inhibitors* / pharmacology
Molecular Structure
Structure-Activity Relationship
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology

Substances

Caffeic Acids
Cinnamates
Lipoxygenase Inhibitors
Triazoles
caffeic acid