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New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition
Joint Authors
Touaibia, Mohamed
Roy, Pierre-Philipe
Faye, Diene
Blanchard, Sébastien
Cormier, Marc
Doiron, Jérémie A.
Surette, Marc E.
Source
Issue
Vol. 2017, Issue 2017 (31 Dec. 2017), pp.1-11, 11 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2017-05-04
Country of Publication
Egypt
No. of Pages
11
Main Subjects
Abstract EN
Leukotrienes are biosynthesized by the conversion of arachidonic acid by 5-Lipoxygenase and play a key role in many inflammatory disorders.
Inspired by caffeic acid phenylethyl ester (CAPE) (2) and an analog carrying a triazole substituted by cinnamoyl and 5-LO inhibitors recently reported by our team, sixteen new CAPE analogs bearing substituted triazole were synthesized by copper catalyzed Huisgen 1,3-dipolar cycloaddition.
Compound 10e, an analog bearing p-CF3 phenethyl substituted triazole, was equivalent to CAPE (2) but clearly surpassed Zileuton (2), the only approved 5-LO inhibitor.
Substitution of the phenethyl moiety by cyclohexylethyl, as with 12g, clearly increased 5-LO inhibition which confirms the importance of hydrophobic interactions.
Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds.
Overall, this work highlights the relevance of exploring polyphenolic compounds as leukotrienes biosynthesis inhibitors.
American Psychological Association (APA)
Roy, Pierre-Philipe& Faye, Diene& Blanchard, Sébastien& Cormier, Marc& Doiron, Jérémie A.& Surette, Marc E.…[et al.]. 2017. New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition. Journal of Chemistry،Vol. 2017, no. 2017, pp.1-11.
https://search.emarefa.net/detail/BIM-1171548
Modern Language Association (MLA)
Roy, Pierre-Philipe…[et al.]. New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition. Journal of Chemistry No. 2017 (2017), pp.1-11.
https://search.emarefa.net/detail/BIM-1171548
American Medical Association (AMA)
Roy, Pierre-Philipe& Faye, Diene& Blanchard, Sébastien& Cormier, Marc& Doiron, Jérémie A.& Surette, Marc E.…[et al.]. New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition. Journal of Chemistry. 2017. Vol. 2017, no. 2017, pp.1-11.
https://search.emarefa.net/detail/BIM-1171548
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1171548