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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.

ABSTRACT: 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.

SUBMITTER: Veselovska L

PROVIDER: S-EPMC7557996 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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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.

Veselovská Lucia L Pohl Radek R Tloušt Ová Eva E Gurská Soňa S Džubák Petr P Hajdúch Marián M Hocek Michal M

ACS omega 20201002 40

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 acti ...[more]

PMID: 33073155

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