Synthesis and biological activity of hydroxycinnamoyl containing antiviral drugs
| Autor: | G Maya Chochkova, Lubomira Nikolaeva-Glomb, S Tsenka Milkova, P Assya Georgieva, I Galya Ivanova, N. Nikolova, Luchia Mukova |
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| Přispěvatelé: | Maya G Chochkova, Tsenka Milkova, Lubomira Nikolaeva Krumova-Glomb, Galya I Ivanova |
| Rok vydání: | 2014 |
| Předmět: |
Catechol
Rimantadine DPPH Stereochemistry Tyrosinase Amantadine antioxidant activity Biological activity General Chemistry anti-influenza activity N-hydroxycinnamoylamides lcsh:Chemistry chemistry.chemical_compound lcsh:QD1-999 chemistry Amide Caffeic acid medicine monophenolase activity influenza antivirals mushroom tyrosinase medicine.drug |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 79, Iss 5, Pp 517-526 (2014) |
| ISSN: | 1820-7421 0352-5139 |
| DOI: | 10.2298/jsc130222103c |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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