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Competing interests during the key N-glycosylation of 6-chloro-7-deaza-7-iodopurine for the synthesis of 7-deaza-2'-methyladenosine using Vorbruggen conditions

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Autor(es):
Naciuk, Fabricio Fredo ; Nascimento, Andrey Fabricio Ziem ; Rocha, Rebeca Paiva Froes ; Rustiguel, Joane Kathelen ; Coimbra, Lais Durco ; Marques, Rafael Elias ; Bruder, Marjorie
Número total de Autores: 7
Tipo de documento: Artigo Científico
Fonte: RONTIERS IN CHEMISTR; v. 11, p. 9-pg., 2023-03-23.
Resumo

A short 3-step synthesis of the antiviral agent 7DMA is described herein. The nature of a major by-product formed during the key N-glycosylation of 6-chloro-7-deaza-7-iodopurine with perbenzoylated 2-methyl-ribose under Vorbruggen conditions was also investigated. Spectroscopic analyses support that the solvent itself is converted into a nucleophilic species competing with the nucleobase and further reacting with the activated riboside in an unanticipated fashion. These findings call for a revision of reaction conditions when working with weakly reactive nucleobases in the presence of Lewis acids. 7DMA thus obtained was evaluated for its efficacy against an emerging flavivirus in vitro. (AU)

Processo FAPESP: 21/05519-0 - Entendendo o papel do recrutamento e ativação de neutrófilos em doenças arbovirais
Beneficiário:Rafael Elias Marques Pereira Silva
Modalidade de apoio: Auxílio à Pesquisa - Regular
Processo FAPESP: 18/10990-1 - Caracterização e potencial terapêutico de quimiocinas em sepse e encefalite induzida por Flavivirus
Beneficiário:Rafael Elias Marques Pereira Silva
Modalidade de apoio: Auxílio à Pesquisa - Regular