New zileuton-hydroxycinnamic acid hybrids: synthesis and structure-activity relationship towards 5-lipoxygenase inhibition was written by Chiasson, Audrey Isabel;Robichaud, Samuel;Moutombi, Fanta J. Ndongou;Hebert, Mathieu P. A.;Mbarik, Maroua;Surette, Marc E.;Touaibia, Mohamed. And the article was included in Molecules in 2020.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:
A novel series of zileuton-hydroxycinnamic acid hybrids I (R1 = H, OH, OMe; n = 0, 1, 2, 3), II (R2 = C6H5, 4-OHC6H4, 2,6-(CH3)2C6H3, etc.) and III (R3 = H, OH, OMe; R4 = H, OH, OMe; R5 = H, OMe) were synthesized and screened as 5-lipoxygenase (5-LO) inhibitors in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Zileuton’s IV benzo[b]thiophene and hydroxyurea subunits combined with hydroxycinnamic acid esters’ ester linkage and phenolic acid moieties were investigated. Compound II (R2 = 3,5-(OMe)2-4-OHC6H2), bearing zileuton’s IV benzo[b]thiophene and sinapic acid phenethyl ester’s V 濞?濞?unsaturated phenolic acid moiety II (R2 = 3,5-(OMe)2-4-OHC6H2), was shown to be equipotent to zileuton IV, the only clin. approved 5-LO inhibitor, in stimulated HEK293 cells. Compound II (R2 = 3,5-(OMe)2-4-OHC6H2) was three times as active as zileuton IV for the inhibition of 5-LO in PMNL. Compound III (R3 = OMe, R4 = OH, R5 = OMe), bearing the same sinapic acid (3,5-dimethoxy-4-hydroxy substitution) moiety as II (R2 = 3,5-(OMe)2-4-OHC6H2), combined with zileuton’s IV hydroxyurea subunit was inactive. This result shows that the zileuton’s IV benzo[b]thiophene moiety is essential for the inhibition of 5-LO product biosynthesis with hydrids. Unlike zileuton IV, compound II (R2 = 3,5-(OMe)2-4-OHC6H2) formed two 闁?闁?interactions with Phe177 and Phe421 as predicted when docked into 5-LO. Compound II (R2 = 3,5-(OMe)2-4-OHC6H2) was the only docked ligand that showed a 闁?闁?interaction with Phe177 which may play a part in product specificity as reported. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene).
1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Quality Control of 1-(2-Bromoethyl)-4-methoxybenzene
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary