ArticleInternational journal of medicinal chemistry2014
Clicked cinnamic/caffeic esters and amides as radical scavengers and 5-lipoxygenase inhibitors.
Article in International journal of medicinal chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 6 citations in OpenAlex.
- A molecular modeling and machine learning-based approach for the identification of potential human ALOX15 inhibitors.Journal of molecular modeling · 2026Article
- Bioactive compounds in European ferns: inhibition of pro-inflammatory enzymes and cytotoxic effects on cancer cells.BMC complementary medicine and therapies · 2026Article
- Synthesis of Caffeoyl-Prolyl-Histidyl-Xaa Derivatives and Evaluation of Their Activities and Stability upon Long-Term Storage.International journal of molecular sciences · 2021Article
- Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties.International journal of medicinal chemistry · 2019Review
- New Hydroxycinnamic Acid Esters as Novel 5-Lipoxygenase Inhibitors That Affect Leukotriene Biosynthesis.Mediators of inflammation · 2017Article
- CAPE Analogs Induce Growth Arrest and Apoptosis in Breast Cancer Cells.Molecules (Basel, Switzerland) · 2015Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.