Chemistry - A European Journal p. 13002 - 13015 (2020)
Update date:2022-08-11
Topics:
D?ubák, Petr
Gurská, Soňa
Hajdúch, Marián
Hocek, Michal
Hodek, Ond?ej
Klepetá?ová, Blanka
Kudlová, Natálie
Li?ková, Barbora
Medvedíková, Martina
Mertlíková-Kaiserová, Helena
Milisavljevic, Nemanja
Perlíková, Pavla
Pohl, Radek
Tichy, Michal
Tlou??ová, Eva
Tryl?ová, Jana
Veselovská, Lucia
All four isomeric series of novel 4-substituted pyrido-fused 7-deazapurine ribonucleosides possessing the pyridine nitrogen atom at different positions were designed and synthesized. The total synthesis of each isomeric fused heterocycle through multistep heterocyclization was followed by glycosylation and derivatization at position 4 by cross-coupling reactions or nucleophilic substitutions. All compounds were tested for cytostatic and antiviral activity. The most active were pyrido[4′,3′:4,5]pyrimidine nucleosides bearing MeO, NH2, MeS, or CH3 groups at position 4, which showed submicromolar cytotoxic effects and good selectivity for cancer cells. The mechanism involved activation by phosphorylation and incorporation to DNA where the presence of the modified ribonucleosides causes double-strand breaks and apoptosis.
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