Department of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi Arabia.
Department of Chemistry, College of Science, King Saud University, P.O Box 2455, Riyadh 11451, Saudi Arabia.
Bioorg Chem. 2020 Jun;99:103799. doi: 10.1016/j.bioorg.2020.103799. Epub 2020 Mar 26.
A series of structurally intriguing novel class of spiropyrrolidine tethered quinoxaline heterocyclic hybrids has been achieved in excellent yields employing ionic liquid accelerated multicomponent 1,3-dipolar cycloaddition reaction strategy. β-Nitrostyrenes were used as dipolarophiles, while the 1,3-dipole component was the azomemthine ylide, generated in situ from indenoquinoxaline and l-phenylalanine. The reaction provided three new bonds and four contiguous stereocenter with full distereomeric control. In vitro activity of these spiroheterocyclic hybrids against Mycobacterium tuberculosis H37Rv using MABA assay revealed that the compound with nitro group on the phenyl ring is the most active candidate (1.56 µg/mL) among the other analogues of the series and has an activity similar to that of the standard drug, Ethambutol.
采用离子液体加速的多组分 1,3-偶极环加成反应策略，以优异的收率得到了一系列结构有趣的新型螺吡咯烷连接的喹喔啉杂环杂合体。β-硝基苯乙烯用作偶极子，而 1,3-偶极子组分是亚氨基叶立德，由茚并喹喔啉和 L-苯丙氨酸原位生成。该反应提供了三个新键和四个连续的立体中心，具有完全的立体异构体控制。使用 MABA 测定法对这些螺杂环杂合体对结核分枝杆菌 H37Rv 的体外活性表明，苯环上带有硝基的化合物是该系列其他类似物中最具活性的候选物（1.56µg/mL），其活性与标准药物乙胺丁醇相似。
