N-(9,10-Dioxo-9,10-dihydroanthracen-1(2)-yl)-2-(R-thio) Acetamides: Synthesis, Antioxidant and Antiplatelet Activity

Authors

  • Maryna Stasevych Lviv Polytechnic National University, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, 79013, Lviv http://orcid.org/0000-0001-5042-4133
  • Viktor Zvarych Lviv Polytechnic National University, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, 79013, Lviv http://orcid.org/0000-0003-3036-0050
  • Olena Yaremkevych Lviv Polytechnic National University, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, 79013, Lviv http://orcid.org/0000-0001-7621-2200
  • Mykhaylo Vovk Department of Chemistry of Functional Heterocyclic Systems, Institute of Organic Chemistry of National Academy of Sciences of Ukraine, 02660 Kyiv http://orcid.org/0000-0003-1753-3535
  • Alla Vaskevych Department of Chemistry of Functional Heterocyclic Systems, Institute of Organic Chemistry of National Academy of Sciences of Ukraine, 02660 Kyiv http://orcid.org/0000-0003-0370-6626
  • Tetiana Halenova Educational and Scientific Center "Institute of Biology and Medicine", Taras Shevchenko National University of Kyiv, 01601, Kyiv http://orcid.org/0000-0003-2973-2646
  • Olexii Savchuk Educational and Scientific Center "Institute of Biology and Medicine", Taras Shevchenko National University of Kyiv, 01601, Kyiv http://orcid.org/0000-0003-3621-6981

DOI:

https://doi.org/10.17344/acsi.2022.7463

Keywords:

N-(9, 10-dioxo-9, 10-dihydroanthracen-1(2)-yl)-2-(R-thio) acetamides, free-radical oxidation markers, antioxidant activity, antiplatelet activity, structure-activity relationship

Abstract

The synthesis of new N-(9,10-dioxo-9,10-dihydroanthracen-1(2)-yl)-2-(R-thio) acetamides was carried out using reaction of 2-chloro-N-(9,10-dioxo-9,10-dihydroanthracene-1(2)-yl)acetamides with functionalized thiols in the presence of potassium carbonate in N,N-dimethylformamide (DMF) at room temperature. Evaluation of the synthesized compounds on such indicators of radical scavenging activity as lipid peroxidation (LP) and oxidative modification of proteins (OMP) in vitro in rat liver homogenate was carried out. It was determined that the compounds with a substituent in the first position of anthracedione core showed better antioxidant properties than their isomers with a substituent in the second position. The compounds 6 and 7 with the best indicators of radical-scavenging activity were determined. Antioxidant effect in OMP processes was also determined for compound 10. The antiplatelet activity study in vitro revealed compound 10 with the inhibited effect of ADP-induced aggregation

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Published

26.09.2022

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Section

Organic chemistry