Chiasson, Audrey Isabel published the artcileNew zileuton-hydroxycinnamic acid hybrids: synthesis and structure-activity relationship towards 5-lipoxygenase inhibition, COA of Formula: C9H10O3, the main research area is benzothiophene hydroxycinnamic acid preparation SAR lipoxygenase inhibition mol docking; radical scavenging activity pharmacokinetic study; 5-Lipoxygenase inhibitors; anti-leukotrienes; hydroxyurea; inflammation; sinapic acid; zileuton.
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 α,α-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 π-π 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 π-π interaction with Phe177 which may play a part in product specificity as reported.
Molecules published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, COA of Formula: C9H10O3.
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem