Synthesis of novel cinnamanilides as potential immunosuppressive agents

A series of new cinnamanilides (6–40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 ± 0.33 and 0.94 ± 0.13 μM) without significant cytotoxicity.

Graphical abstractA series of new cinnamanilides were synthesized and their immunosuppressive activities were evaluated. Compunds 37 and 38 exhibited most potent immunosuppressive activity (IC50 = 1.77 ± 0.33 and 0.94 ± 0.13 μM).Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 35 novel cinnamanilides were synthesized for the first time. ► The immunosuppressive activity and cytotoxicity of these compounds were evaluated. ► Compounds 37 and 38 exhibited most potent immunosuppressive activity. ► These compounds did not exhibit significant cytotoxicity. ► This study may be helpful for the discovery of new immunosuppressant leads.