Structure-Activity Relationship Studies of New Sinapic Acid Phenethyl Ester Analogues Targeting the Biosynthesis of 5-Lipoxygenase Products: The Role of Phenolic Moiety, Ester Function, and Bioisosterism was written by Touaibia, Mohamed;Faye, Diene Codou;Doiron, Jeremie A.;Chiasson, Audrey Isabel;Blanchard, Sebastien;Roy, Pierre-Philippe;Surette, Marc E.. And the article was included in Journal of Natural Products in 2022.Computed Properties of C9H11BrO This article mentions the following:
Sinapic acid is found in many edible plants and fruits, such as rapeseed, where it is the predominant phenolic compound New sinapic acid phenethyl ester (SAPE) analogs were synthesized and screened as inhibitors of the biosynthesis of 5-lipoxygenase (5-LO) in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Inhibition of leukotriene biosynthesis catalyzed by 5-LO is a validated therapeutic strategy against certain inflammatory diseases and allergies. Unfortunately, the only inhibitor approved to date has limited clin. use because of its poor pharmacokinetic profile and liver toxicity. With the new analogs synthesized in this study, the role of the phenolic moiety, ester function, and bioisosterism was investigated. Several of the 34 compounds inhibited the biosynthesis of 5-LO products, and 20 compounds were 2-11 times more potent than zileuton in PMNL, which are important producers of 5-LO products. Compounds 5i (I)(IC50: 0.20 μM), 5l (II) (IC50: 0.20 μM), and 5o (III)(IC50: 0.21 μM) bearing 4-trifluoromethyl, Me, or methoxy substituent at meta-position of the phenethyl moiety were 1.5 and 11.5 times more potent than SAPE (IC50: 0.30 μM) and zileuton (IC50: 2.31 μM), resp. Addnl., compound 9 (IC50: 0.27 μM), which was obtained after acetylation of the 4-hydroxyl of SAPE, was equivalent to SAPE and 8 times more active than zileuton. Furthermore, compound 20b (IV) (IC50: 0.27 μM) obtained after the bioisosteric replacement of the ester function of SAPE by the 1,2,4-oxadiazole heterocycle was equivalent to SAPE and 8 times more active than zileuton. Thus, this study provides a basis for the rational design of new mols. that could be developed further as anti 5-LO therapeutics. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Computed Properties of C9H11BrO).
1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Computed Properties of C9H11BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary