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Synthesis of New Imidazopyridine Nucleoside Derivatives Designed as Maribavir Analogues.

ABSTRACT: The strong inhibition of Human Cytomegalovirus (HCMV) replication by benzimidazole nucleosides, like Triciribine and Maribavir, has prompted us to expand the structure-activity relationships of the benzimidazole series, using as a central core the imidazo[4,5-b]pyridine scaffold. We have thus synthesized a number of novel amino substituted imidazopyridine nucleoside derivatives, which can be considered as 4-(or 7)-aza-d-isosters of Maribavir and have evaluated their potential antiviral activity. The target compounds were synthesized upon glycosylation of suitably substituted 2-aminoimidazopyridines, which were prepared in six steps starting from 2-amino-6-chloropyridine. Even if the new compounds possessed only a slight structural modification when compared to the original drug, they were not endowed with interesting antiviral activity. Even so, three derivatives showed promising cytotoxic potential.

SUBMITTER: Papadakis G

PROVIDER: S-EPMC7582934 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Synthesis of New Imidazopyridine Nucleoside Derivatives Designed as Maribavir Analogues.

Papadakis Georgios G Gerasi Maria M Snoeck Robert R Marakos Panagiotis P Andrei Graciela G Lougiakis Nikolaos N Pouli Nicole N

Molecules (Basel, Switzerland) 20201003 19

The strong inhibition of Human Cytomegalovirus (HCMV) replication by benzimidazole nucleosides, like Triciribine and Maribavir, has prompted us to expand the structure-activity relationships of the benzimidazole series, using as a central core the imidazo[4,5-b]pyridine scaffold. We have thus synthesized a number of novel amino substituted imidazopyridine nucleoside derivatives, which can be considered as 4-(or 7)-aza-d-isosters of Maribavir and have evaluated their potential antiviral activity. ...[more]

PMID: 33022923

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