Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines

0534197 - ÚOCHB 2021 RIV US eng J - Článek v odborném periodiku
Veselovská, Lucia - Pohl, Radek - Tloušťová, Eva - Gurská, S. - Džubák, P. - Hajdúch, M. - Hocek, Michal
Pyrido-Fused Deazapurine Bases: Synthesis and Glycosylation of 4-Substituted 9H-Pyrido[2′,3′:4,5]- and Pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidines.
ACS Omega. Roč. 5, č. 40 (2020), s. 26278-26286. ISSN 2470-1343. E-ISSN 2470-1343
Grant CEP: GA ČR(CZ) GA19-08124S; GA MŠMT(CZ) LM2015064
Grant ostatní: AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institucionální podpora: RVO:61388963
Klíčová slova: Thymidylate synthase inhibitors * receptor tyrosine kinase * biological activity
Obor OECD: Organic chemistry
Impakt faktor: 3.512, rok: 2020
Způsob publikování: Open access
https://doi.org/10.1021/acsomega.0c04302

Two isomeric sets of 4-substituted pyridopyrrolopyrimidine nucleobases were prepared through nucleophilic substitutions or cross-coupling reactions of 4-chloropyridopyrrolopyrimidines. The corresponding 4-amino-pyridopyrrolopyrimidines were glycosylated with 5-O-tritylribose using the modified Mitsunobu protocol. Several examples of the title heterocycles showed blue or green fluorescence. Testing of the pyridopyrrolopyrimidine nucleobases for the cytotoxic effect revealed micromolar activity of 4-benzofuryl derivatives in both series, preferentially in multidrug-resistant cancers.
Trvalý link: http://hdl.handle.net/11104/0312441