65547-81-1Relevant 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.
Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells
Shaw, Arthur Y.,Chang, Chun-Yi,Liau, Hao-Han,Lu, Pei-Jung,Chen, Hui-Ling,Yang, Chia-Ning,Li, Hao-Yi
experimental part, p. 2552 - 2562 (2009/09/30)
A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC50 value of 28.9 μM against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 μM against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 μM induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q2 of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones.
New photochemical approaches to the synthesis of chromones
Alvaro, Mercedes,Garcia, Hermenegildo,Iborra, Sara,A. Miranda, Miguel,Primo, Jaime
, p. 143 - 148 (2007/10/02)
Irradiation of the p-methoxyphenyl and p-methylphenyl esters of 2-butynoic, propynoic, 3-(ethylenedioxy)butanoic, 3,3-dimethoxypropanoic and 3-oxobutanoic acids (1-3) affords the corresponding photo-Fries products 4-6. Compound 5a is converted in part into the acetophenone 7a, by way of a Norrish type II photo-reaction, while compound 6a is reluctant to undergo this process, in spite of the fact that it also possess γ-carbonyl hydrogen atoms. From the preparative point of view, the photorearrangement of the esters 1a-d and 2a,c-d is exploitable, while that of 3a proceeds with a lower yield. The differences found in the photochemical behaviour of 2a and 3a show the sharp influence of the acetal group on the course of the reaction. Compounds 4-6 are representative model compounds valuable as direct chromone precursors; in fact, they can be readily cyclized to the chromones 10 under basic or acidic conditions.
