Seven N-hydroxycinnamoyl amides were synthesized by EDC/HOBt coupling of the
corresponding substituted cinnamic acids (p-coumaric-, ferulic-, sinapic-
and caffeic acids) with influenza antivirals (amantadine, rimantadine and
oseltamivir). DPPH (1,1-diphenyl-2-picrylhydrazyl) scavenging abilities and
the inhibitory effect on mushroom tyrosinase activity (using L-tyrosine as
the substrate) were investigated in vitro. Amongst the synthesized
compounds, N-[(E)-3-(3?,4?-dihydroxyphenyl)-2-propenoyl]oseltamivir (1) and
N-[(E)-3-(3?,4?-dihydroxyphenyl)-2-propenoyl]rimantadine (4), containing
catechol moiety, exhibited the most potent DPPH radical-scavenging activity.
Amide (1) displayed also tyrosinase inhibitory effect toward L-tyrosine as
the substrate (~50%). Due to its biological activities revealed so far
compound (1) can be considered as a promising candidate for a cosmetic
ingredient. The synthesized compounds were also investigated for their in
vitro inhibitory activity against the replication of influenza virus A
(H3N2).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.