Microwave‐Assisted Multicomponent Synthesis of New 6‐Arylated 5‐Hydroxy‐benzo[ <i>a</i> ]phenazine Derivatives and Their Potential Anti‐inflammatory Activity
Ha Thanh Nguyen, Nguyễn Thị Thu Hà, Julien Braire, Tuyet Anh Dang Thi, Tuyen Nguyen Van
Abstract
Abstract A convenient two step “one‐pot” four‐component synthetic approach was developed for the synthesis of new 6‐arylated 5‐hydroxy‐benzo[ a ]phenazine derivatives using 2‐hydroxy‐1,4‐naphthoquinone, a variety of aromatic aldehydes, benzene‐1,2‐diamine, and tetronic acid. In all cases, the synthesis proceeded via three key steps including condensation, Michael addition, and tautomerization. The structure of synthesized compounds was elucidated by spectral data. The inhibitory effect of newly synthesized compounds on nitric oxide (NO) production in lipopolysaccharide (LPS)‐ stimulated murine macrophage RAW 264.7 cells was assessed. All products exhibited the highly potential NO production inhibition activity with the IC 50 values in the range of 3.68–12.14 μM, indicating the critical role of these compounds in the development of potential anti‐inflammation agents.