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

[Image: see text] 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...

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Autores principales: Veselovská, Lucia, Pohl, Radek, Tloušt′ová, Eva, Gurská, Soňa, Džubák, Petr, Hajdúch, Marián, Hocek, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7557996/
https://www.ncbi.nlm.nih.gov/pubmed/33073155
http://dx.doi.org/10.1021/acsomega.0c04302
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author Veselovská, Lucia
Pohl, Radek
Tloušt′ová, Eva
Gurská, Soňa
Džubák, Petr
Hajdúch, Marián
Hocek, Michal
author_facet Veselovská, Lucia
Pohl, Radek
Tloušt′ová, Eva
Gurská, Soňa
Džubák, Petr
Hajdúch, Marián
Hocek, Michal
author_sort Veselovská, Lucia
collection PubMed
description [Image: see text] 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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spelling pubmed-75579962020-10-16 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 Pohl, Radek Tloušt′ová, Eva Gurská, Soňa Džubák, Petr Hajdúch, Marián Hocek, Michal ACS Omega [Image: see text] 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. American Chemical Society 2020-10-02 /pmc/articles/PMC7557996/ /pubmed/33073155 http://dx.doi.org/10.1021/acsomega.0c04302 Text en © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Veselovská, Lucia
Pohl, Radek
Tloušt′ová, Eva
Gurská, Soňa
Džubák, Petr
Hajdúch, Marián
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7557996/
https://www.ncbi.nlm.nih.gov/pubmed/33073155
http://dx.doi.org/10.1021/acsomega.0c04302
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