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 - Journal Article
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
R&D Projects: GA ČR(CZ) GA19-08124S; GA MŠMT(CZ) LM2015064
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : Thymidylate synthase inhibitors * receptor tyrosine kinase * biological activity
OECD category: Organic chemistry
Impact factor: 3.512, year: 2020
Method of publishing: 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.
Permanent Link: http://hdl.handle.net/11104/0312441