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

• Published in: Acta chimica Slovenica Vol. 69; no. 3; pp. 584 - 595
• Main Authors: Stasevych, Maryna, Zvarych, Viktor, Yaremkevych, Olena, Vovk, Mykhaylo, Vaskevych, Alla, Halenova, Tetiana, Savchuk, Olexii
• Format: Journal Article
• Language: English
• Published: Slovenian Chemical Society 26.09.2022
• Subjects: antioxidant activity; antiplatelet activity; free-radical oxidation markers; n-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-(r-thio) acetamides; structure-activity relationship
• ISSN: 1580-3155; 1318-0207; 1580-3155
• DOI: 10.17344/acsi.2022.7463

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.