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- Title
Synthesis and biological activity of hydroxycinnamoyl-containing antiviral drugs.
- Authors
CHOCHKOVA, MAYA G.; GEORGIEVA, ASSYA P.; IVANOVA, GALYA I.; NIKOLOVA, NADYA; MUKOVA, LUCHIA; NIKOLAEVA-GLOMB, LUBOMIRA; MILKOVA, TSENKA S.
- Abstract
Seven N-hydroxycinnamoyl amides were synthesized by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide/1-hydroxybenzotriazole (EDC/HOBt) coupling of the corresponding substituted cinnamic acids (p-coumaric-, ferulic-, sinapic- and caffeic acids) with influenza antivirals (amantadine, rimantadine and oseltamivir). The 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 a catechol moiety, exhibited the most potent DPPH radical-scavenging activity. Amide (1) also displayed tyrosinase inhibitory effect toward L-tyrosine as the substrate (≈50%). The synthesized compounds were also investigated for their in vitro inhibitory activity against the replication of influenza virus A (H3N2).
- Subjects
CINNAMOYL compounds; ANTIVIRAL agent synthesis; CAFFEIC acid; AMANTADINE; RIMANTADINE; INFLUENZA A virus
- Publication
Journal of the Serbian Chemical Society, 2014, Vol 79, Issue 5, p517
- ISSN
0352-5139
- Publication type
Article
- DOI
10.2298/JSC130222103C