3450-77-9Relevant academic research and scientific papers
A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin
Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Salimi, Alireza,Eshghi, Hossein
, p. 1125 - 1132 (2018/03/02)
Inflammations, sensitivities, and some cancers in mammals are intimately linked to the activity of lipo-oxygenase enzymes. Owing to the importance of these enzymes, mechanistic studies, product analysis, and synthesis of inhibitors have expanded. In this study, a series of hydroxycoumarins, methoxy-3-hydroxy coumarins, and 7-alkoxy-3-hydroxy coumarins were synthesized and evaluated as potential inhibitors of human 15-LOX-1. Among the synthetic coumarins, 7-methoxy-3-hydroxycoumarin derivative demonstrated potent inhibitory activity and the compound, 5f, showed the best result. Radical scavenging assessment, IC50, HNMR, and DPPH bleaching results indicate that the electronic properties are the major factors for the lipo-oxygenase inhibition potency of the synthetic coumarins. Based on the theoretical studies, it was suggested that the mesomeric effect of the substituent at the seventh position of the benzene ring is one of the major factors in the stability of the oxy-radical intermediate.
New efficient synthesis of pyrido[2,3-c] and pyrido[3,2-c]coumarin derivatives
Pavé, Grégoire,Chalard, Pierre,Viaud-Massuard, Marie-Claude,Troin, Yves,Guillaumet, Gérald
, p. 987 - 990 (2007/10/03)
Various substituted pyrido[2,3-c] and pyrido[3,2-c]coumarins are efficiently prepared in three steps from 3- and 4-hydroxycoumarins, respectively and protected β-aminoketones.
Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide
Dupont, Romain,Cotelle, Philippe
, p. 597 - 600 (2007/10/03)
(Z)-Mono, di or trimethoxyphenyl-2-hydroxypropenoic acids 1a-d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a-d when treated with boron tibromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs, and 3-hydroxycoumarins 3 and benzofuran-2-carboxylic acids 4 can be obtained. 3-Hydroxycoumarin 3a can also be obtained almost quatitatively from the reaction of methyl 3-(2-methoxyphenyl)-2,3-epoxypropanoate with boron tribromide.
