1033328-73-2Relevant articles and documents
Synthesis and biological evaluation of 3-styrylchromone derivatives as selective monoamine oxidase B inhibitors
Takao, Koichi,Takemura, Yuri,Nagai, Junko,Kamauchi, Hitoshi,Hoshi, Kaori,Mabashi, Ryo,Uesawa, Yoshihiro,Sugita, Yoshiaki
, (2021/06/15)
A series of 3-styrylchromone derivatives was synthesized and evaluated for monoamine oxidase (MAO) A and B inhibitory activities. Most of all derivatives inhibited MAO-B selectively, except compound 21. Compound 19, which had a methoxy group at R2 on the chromone ring and chlorine at R4 on phenyl ring, potently inhibited MAO-B, with an IC50 value of 2.2 nM. Compound 1 showed the highest MAO-B selectivity, with a selectivity index of >3700. Further analysis of these compounds indicated that compounds 1 and 19 were reversible and mixed-type MAO-B inhibitors, suggesting that their mode of action may be through tight-binding inhibition to MAO-B. Quantitative structure–activity relationship (QSAR) analyses of the 3-styrylchromone derivatives were conducted using their pIC50 values, through Molecular Operating Environment (MOE) and Dragon. There were 1796 descriptors of MAO-B inhibitory activity, which showed significant correlations (P 50 value index exhibited a determination coefficients (R2) of 0.972 and a Leave-One-Out cross-validated determination coefficients (Q2) of 0.914. These data suggest that the 3-styrylchromone derivatives assessed herein may be suitable for the design and development of novel MAO inhibitors.
Efficient Heck cross-coupling of 3-iodo-benzopyrones with olefins under microwave irradiation without phosphine
Zhang, Yikai,Lv, Zhiliang,Zhong, Hanyu,Zhang, Mingfeng,Zhang, Tao,Zhang, Wannian,Li, Ke
, p. 9777 - 9787 (2012/11/07)
An efficient and effective microwave-assisted Heck cross-coupling of different terminal olefins with various 3-iodo-benzopyrones including sterically hindered, electron-rich, electron-neutral, and electron-deficient is developed. It proceeded faster and g
Microwave-induced synthesis and regio- and stereoselective epoxidation of 3-styrylchromones
Patonay, Tamas,Kiss-Szikszai, Attila,Silva, Vera M. L.,Silva, Artur M. S.,Pinto, Diana C. G. A.,Cavaleiro, Jose A. S.,Jeko, Jozsef
body text, p. 1937 - 1946 (2009/04/04)
The microwave-assisted solvent-free synthesis of (E)-3-styrylchromones from 3-formylchromones and phenylmalonic acid on sodium acetate support has been developed; the method affords the styryl derivatives in moderate to good yields and with complete diastereoselectivity. Protocols for the highly regioselective epoxidation of (E)- and (Z)-3-styrylchromones have been elaborated. Treatment of the alkenes with dimethyldioxirane led to the exclusive formation of 3-(3-aryloxiran-2-yl)chromones with complete diastereoselectivity, whereas treatment with hydrogen peroxide under alkaline conditions afforded the corresponding 2,3-epoxy-3-styrylchromanones as the only products. Epoxidation performed in the presence of chiral, nonracemic cinchona-alkaloid-based quaternary ammonium salts allowed the synthesis of enantiomerically enriched 2,3-epoxy-3-styrylchromanones, but with only moderate ee values. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.