71835-85-3Relevant articles and documents
Catechol-based inhibitors of bacterial urease
Pagoni, Aikaterini,Daliani, Theohari,Macegoniuk, Katarzyna,Vassiliou, Stamatia,Berlicki, ?ukasz
supporting information, p. 1085 - 1089 (2019/03/07)
Targeted covalent inhibitors of urease were developed on the basis of the catechol structure. Forty amide and ester derivatives of 3,4-dihydroxyphenylacetic acid, caffeic acid, ferulic acid and gallic acid were obtained and screened against Sporosarcinia pasteurii urease. The most active compound, namely propargyl ester of 3,4-dihydroxyphenylacetic acid exhibited IC50 = 518 nM andkinact/Ki = 1379 M?1 s?1. Inhibitory activity of this compound was better and toxicity lower than those obtained for the starting compound – catechol. The molecular modelling studies revealed a mode of binding consistent with structure-activity relationships.
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.
Synthesis of caffeic acid phenethyl ester analogues and their cytotoxicities against human cancer cells
Wang, Yan-Hui,Li, Qu-Sheng,Wang, Peng-Long,Xu, Kuo,Cheng, Ya-Tao,Xu, Xin,Li, Qiang,Zhang, Yu-Zhong,Lei, Hai-Min
, p. 2686 - 2690 (2014/06/09)
Although caffeic acid phenethyl ester exhibits strong antitumor property, but its pharmacophore has not been elaborated clearly as yet. Seventeen caffeic acid phenethyl ester analogues were synthesized via simple and easy procedures and their antiprolifer
