100981-80-4Relevant articles and documents
Sinapic acid phenethyl ester as a potent selective 5-lipoxygenase inhibitor: Synthesis and structure–activity relationship
Touaibia, Mohamed,Hébert, Martin J. G.,Levesque, Natalie A.,Doiron, Jérémie A.,Doucet, Marco S.,Jean-Fran?ois, Jacques,Cormier, Marc,Boudreau, Luc H.,Surette, Marc E.
, p. 1876 - 1887 (2018/08/06)
Given the hepatotoxicity and an unfavorable pharmacokinetic profile of zileuton (Zyflo), currently the only approved and clinically used 5-Lipoxygenase (5-LO) inhibitor, the search for potent and safe 5-LO inhibitors is highly demanded. The action of several phenolic acid phenethyl esters as potential 5-Lipoxygenase (5-LO) inhibitors has been investigated. For this purpose, a series of 14 phenethyl esters was synthesized and their impact on 5-LO inhibition was evaluated. The effects of position and number of hydroxyl and methoxy groups on the phenolic acid were investigated. The shortening of the linker between the carbonyl and the catechol moiety as well as the presence of the α,β-unsaturated carbonyl group was also explored. The sinapic acid phenethyl ester (10), which can be named SAPE (10) by analogy to caffeic acid phenethyl ester (CAPE), inhibited 5-LO in a concentration-dependent manner and outperformed both zileuton (1) and CAPE (2). With an IC50 of 0.3?μm, SAPE (10) was threefold more potent than CAPE (2) and 10-fold more potent than zileuton (1), the only 5-LO inhibitor approved for clinical use. Unlike CAPE (2), SAPE (10) had no effect on 12-lipoxygenase (12-LO) and less effect on cyclooxygenase 1 (COX-1) which makes it a more selective 5-LO inhibitor.
Design of antibacterial agents: Alkyl dihydroxybenzoates against xanthomonas citri subsp. citri
Nazaré, Ana Carolina,Polaquini, Carlos Roberto,Anselmo, Daiane Bertholin,Regasini, Luis Octavio,Cavalca, Lúcia Bonci,Ferreira, Henrique,Zielinska, Aleksandra,Scheffers, Dirk-Jan,Saiki, Marilia de Freitas Calmon,Monteiro, Diego Alves,Rahal, Paula,Gomes, Eleni
, (2018/11/21)
Xanthomonas citri subsp. citri (Xcc) causes citrus canker, affecting sweet orange-producing areas around the world. The current chemical treatment available for this disease is based on cupric compounds. For this reason, the objective of this study was to design antibacterial agents. In order to do this, we analyzed the anti-Xcc activity of 36 alkyl dihydroxybenzoates and we found 14 active compounds. Among them, three esters with the lowest minimum inhibitory concentration values were selected; compounds 4 (52 μM), 16 (80 μM) and 28 (88 μM). Our study demonstrated that alkyl dihydroxybenzoates cause a delay in the exponential phase. The permeability capacity of alkyl dihydroxybenzoates in a quarter of MIC was compared to nisin (positive control). Compound 28 was the most effective (93.8), compared to compound 16 (41.3) and compound 4 (13.9) by percentage values. Finally, all three compounds showed inhibition of FtsZ GTPase activity, and promoted changes in protofilaments, leading to depolymerization, which prevents bacterial cell division. In conclusion, heptyl dihydroxybenzoates (compounds 4, 16 and 28) are promising anti-Xcc agents which may serve as an alternative for the control of citrus canker.
Synthesis and antiradical/antioxidant activities of caffeic acid phenethyl ester and its related propionic, acetic, and benzoic acid analogues
LeBlanc, Luc M.,Pare, Aurelie F.,Jean-Francois, Jacques,Hebert, Martin J.G.,Surette, Marc E.,Touaibia, Mohamed
, p. 14637 - 14650 (2013/03/13)
Caffeic acid phenethyl ester (CAPE) is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl) propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl) acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.