Clicked CinnamicCaffeic Esters and Amides as Radical Scavengers and 5-Lipoxygenase Inhibitors
Joint Authors
Touaibia, Mohamed
Desjardins, Dany
Poirier, Samuel J.
Jean-François, Jacques
Levesque, Natalie A.
Doiron, Jérémie A.
Boudreau, Luc H.
Surette, Marc E.
Métayer, Benoît
Richard, Ryan R.
Source
International Journal of Medicinal Chemistry
Issue
Vol. 2014, Issue 2014 (31 Dec. 2014), pp.1-12, 12 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2014-02-18
Country of Publication
Egypt
No. of Pages
12
Main Subjects
Abstract EN
5-Lipoxygenase (5-LO) is the key enzyme responsible for the conversion of arachidonic acid to leukotrienes, a class of lipid mediators implicated in inflammatory disorders.
In this paper, we describe the design, synthesis, and preliminary activity studies of novel clicked caffeic esters and amides as radical scavengers and 5-LO inhibitors.
From known 5-LO inhibitor 3 as a lead, cinnamic esters 8a–h and amides 9a–h as well as caffeic esters 15a–h and amides 16a–h were synthesized by Cu(I)-catalyzed [1,3]-dipolar cycloaddition with the appropriate azide precursors and terminal alkynes.
All caffeic analogs are proved to be good radical scavengers (IC50: 10–20 μM).
Esters 15g and 15f possessed excellent 5-LO inhibition activity in HEK293 cells and were equipotent with the known 5-LO inhibitor CAPE and more potent than Zileuton.
Several synthesized esters possess activities rivaling Zileuton in stimulated human polymorphonuclear leukocytes.
American Psychological Association (APA)
Doiron, Jérémie A.& Métayer, Benoît& Richard, Ryan R.& Desjardins, Dany& Boudreau, Luc H.& Levesque, Natalie A.…[et al.]. 2014. Clicked CinnamicCaffeic Esters and Amides as Radical Scavengers and 5-Lipoxygenase Inhibitors. International Journal of Medicinal Chemistry،Vol. 2014, no. 2014, pp.1-12.
https://search.emarefa.net/detail/BIM-509196
Modern Language Association (MLA)
Doiron, Jérémie A.…[et al.]. Clicked CinnamicCaffeic Esters and Amides as Radical Scavengers and 5-Lipoxygenase Inhibitors. International Journal of Medicinal Chemistry No. 2014 (2014), pp.1-12.
https://search.emarefa.net/detail/BIM-509196
American Medical Association (AMA)
Doiron, Jérémie A.& Métayer, Benoît& Richard, Ryan R.& Desjardins, Dany& Boudreau, Luc H.& Levesque, Natalie A.…[et al.]. Clicked CinnamicCaffeic Esters and Amides as Radical Scavengers and 5-Lipoxygenase Inhibitors. International Journal of Medicinal Chemistry. 2014. Vol. 2014, no. 2014, pp.1-12.
https://search.emarefa.net/detail/BIM-509196
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-509196