Author:
Naciuk Fabrício Fredo,Nascimento Andrey Fabricio Ziem,Rocha Rebeca Paiva Froes,Rustiguel Joane Kathelen,Coimbra Lais Durço,Marques Rafael Elias,Bruder Marjorie
Abstract
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 Vorbrüggen 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.
Funder
Fundação de Amparo à Pesquisa do Estado de São Paulo
Ministério da Ciência, Tecnologia e Inovação
Cited by
1 articles.
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