42926-53-4Relevant articles and documents
Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors
Delogu, Giovanna L.,Kumar, Amit,Gatto, Gianluca,Bustelo, Fernando,Saavedra, Lucía M.,Rodríguez-Franco, Maria Isabel,Laguna, Reyes,Vi?a, Dolores
, (2021/01/14)
A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran moiety determine the affinity for MAO-A or MAO-B. The 2-(3-methoxyphenyl)-5-nitrobenzofuran 9 was the most potent MAO-B inhibitor (IC50 = 0.024 μM) identified in this series, whereas 7-nitro-2-phenylbenzofuran 7 was the most potent MAO-A inhibitor (IC50 = 0.168 μM), both acting as reversible inhibitors. The number and position of the methoxyl groups on the 2-phenyl ring, have an important influence on the inhibitory activity. Molecular docking studies confirmed the experimental results and highlighted the importance of key residues in enzyme inhibition.
B(C6F5)3-Catalyzed Hydroarylation of Aryl Alkynes for the Synthesis of 1,1-Diaryl and Triaryl Substituted Alkenes
Chen, Hui,Gao, Liuzhou,Liu, Xueting,Wang, Guoqiang,Li, Shuhua
supporting information, p. 5238 - 5242 (2021/10/19)
A new strategy for the synthesis of 1,1-diaryl and triarylsubstituted alkenes has been developed utilizing B(C6F5)3-catalyzed hydroarylation of alkynes with phenols. The method provides a direct route to ortho-alkenylated phenols with both terminal and internal alkynes. The reactions show excellent regioselectivity, and good stereoselectivity was observed for the hydroarylation of internal alkynes. Computational and experimental studies suggest that for the reaction of internal alkynes and phenols, an acid-catalyzed isomerization mechanism involving two tertiary carbonium ion intermediates is responsible for the formation of Z-triaryl substituted alkenes.
Synthesis of benzofurans from terminal alkynes and iodophenols catalyzed by recyclable palladium nanoparticles supported on N,O-dual doped hierarchical porous carbon under copper- and ligand-free conditions
Ji, Guijie,Duan, Yanan,Zhang, Shaochun,Yang, Yong
, p. 101 - 108 (2018/05/05)
We herein report that a stable and recyclable heterogeneous catalyst, consisting of Pd nanoparticles supported on N,O-dual doped hierarchical porous carbon derived from naturally available and renewable biomass-bamboo shoots, which allows for highly efficient one-pot tandem reaction of o-iodophenols with terminal alkynes to synthesize biologically active 2-benzofuran derivatives under copper- and ligand-free conditions. The catalyst performed superior catalytic performance compared with the analogous Pd/C and supported on other metal oxides under otherwise identical conditions. A broad set of aryl and alkyl terminal alkynes can be effectively coupled /cyclized with various o-iodophenols to afford their corresponding 2-benzofurans in good to high yields with good tolerance of multiple functional groups. Moreover, the catalyst showed good stability and could be reused several times without significant loss of activity.
