76361-69-8Relevant academic research and scientific papers
2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors
Takao, Koichi,Endo, Saki,Nagai, Junko,Kamauchi, Hitoshi,Takemura, Yuri,Uesawa, Yoshihiro,Sugita, Yoshiaki
, (2019/09/30)
A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B inhibitory activity (IC50 = 17 ± 2.4 nM) and the best MAO-B selectivity (IC50 for MAO-A/IC50 for MAO-B = 1500). The mode of inhibition of compound 9 against MAO-B was competitive and reversible. Quantitative structure–activity relationship (QSAR) analyses of the 2-styrylchromone derivatives were conducted using their pIC50 values with the use of Molecular Operating Environment (MOE) and Dragon, demonstrating that the descriptors of MAO-B inhibitory activity and MAO-B selectivity were 1734 and 121, respectively, that showed significant correlations (P 50 value indexes for MAO-B exhibited a determination coefficient (R2) of 0.873 as well as a Leave-One-Out cross-validated determination coefficient (Q2) of 0.675. These data suggested that the 2-styrylchromone structure might be a useful scaffold for the design and development of novel MAO-B inhibitors.
A CONVENIENT SYNTHESIS OF 2-STYRYLCHROMONES BY MODIFIED BAKER-VENKATARAMAN TRANSFORMATION USING PHASE TRANSFER CATALYSIS.
Makrandi, J. K.,Kumari, Vandna
, p. 1919 - 1922 (2007/10/02)
Condensation of 2-hydroxyacetophenones 1 with cinnamic anhydrides 2 in the presence of tetra-n-butyl ammonium hydrogen sulfate in benzene-aqueous potassium carbonate biphase medium give 1-(2-hydroxyphenyl)-5-phenyl-4-pentene-1,3-diones 3 which on cyclodeh
