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 | Zendy

Lucia Veselovská | Zendy; Radek Pohl | Zendy; Eva Tloušťová | Zendy; Soňa Gurská | Zendy; Petr Džubák | Zendy; Marián Hajdúch | Zendy; Michal Hocek | Zendy

Open Access

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

Author(s) -

Lucia Veselovská,

Radek Pohl,

Eva Tloušťová,

Soňa Gurská,

Petr Džubák,

Marián Hajdúch,

Michal Hocek

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

ISSN - 2470-1343

DOI - 10.1021/acsomega.0c04302

Subject(s) - nucleobase , chemistry , stereochemistry , glycosylation , nucleophile , mitsunobu reaction , combinatorial chemistry , organic chemistry , dna , biochemistry , catalysis

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.

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