Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core

Rippel, Rafael; Pinheiro, Luís; Lopes, Mónica; Lourenço, Ana; Ferreira, Luísa M.; Branco, Paula S.

http://hdl.handle.net/10362/105370

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Resumo(s)

The synthesis of an unreported 2-aminopyrrolidine-1-carboxamidine unit is here described for the first time. This unusual and promising structure was attained through the oxidative decarboxylation of amino acids using the pair of reagents, silver(I)/peroxydisulfate (Ag(I)/S2O82−) followed by intermolecular (in the case of L-proline derivative) and intramolecular trapping (in the case of acyl L-arginine) by N-nucleophiles. The L-proline approach has a broader scope for the synthesis of 2-aminopyrrolidine-1-carboxamidine derivatives, whereas the intramolecular cyclization afforded by the L-acylarginines, when applied, results in higher yields. The former allowed the first synthesis of cernumidine, a natural alkaloid isolated in 2011 from Solanum cernuum Vell, as its racemic form.

Descrição

Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UIDB/50006/2020). Grant number SFRH/BD/136692/2018 from FCT/MCTES.

Palavras-chave

Amino acid decarboxylation Cernumidine Cyclic-guanidine Radical decarboxylation Analytical Chemistry Chemistry (miscellaneous) Molecular Medicine Pharmaceutical Science Drug Discovery Physical and Theoretical Chemistry Organic Chemistry