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Hydroxymethyl-Branched Polyhydroxylated Indolizidines: Novel Selective α-Glucosidase Inhibitors.
Boisson, Julien; Thomasset, Amélia; Racine, Emilie; Cividino, Pascale; Banchelin Sainte-Luce, Thomas; Poisson, Jean-François; Behr, Jean-Bernard; Py, Sandrine.
Afiliação
  • Boisson J; †Univ. Grenoble Alpes, DCM, F-38000 Grenoble, France.
  • Thomasset A; ‡CNRS, DCM, F-38000 Grenoble, France.
  • Racine E; †Univ. Grenoble Alpes, DCM, F-38000 Grenoble, France.
  • Cividino P; ‡CNRS, DCM, F-38000 Grenoble, France.
  • Banchelin Sainte-Luce T; †Univ. Grenoble Alpes, DCM, F-38000 Grenoble, France.
  • Poisson JF; ‡CNRS, DCM, F-38000 Grenoble, France.
  • Behr JB; †Univ. Grenoble Alpes, DCM, F-38000 Grenoble, France.
  • Py S; ‡CNRS, DCM, F-38000 Grenoble, France.
Org Lett ; 17(15): 3662-5, 2015 Aug 07.
Article em En | MEDLINE | ID: mdl-26181493
α,α-Disubstituted piperidines and conformationally constrained polyhydroxylated indolizidines bearing a hydroxymethyl substituent in position 8a were synthesized from a readily available l-sorbose-derived ketonitrone. Diastereoselective vinylation under two sets of complementary conditions allowed access to both configurations of the newly formed quaternary stereocenter. Subsequent N-allylation and ring-closing metathesis afforded 8a-branched indolizidines in high yield. The newly prepared iminosugars demonstrated highly potent inhibition of α-glucosidases. Most interestingly, compound 9b exhibits very high selectivity toward this class of enzymes, with an unusual mode of binding.
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piperidinas / Alfa-Glucosidases / Indolizidinas / Inibidores de Glicosídeo Hidrolases Idioma: En Ano de publicação: 2015 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piperidinas / Alfa-Glucosidases / Indolizidinas / Inibidores de Glicosídeo Hidrolases Idioma: En Ano de publicação: 2015 Tipo de documento: Article