Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B (Articolo in rivista)

Type
Label
  • Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.201300103 (literal)
Alternative label
  • Martella, Daniele; Cardona, Francesca; Parmeggiani, Camilla; Franco, Francisco; Tamayo, Juan A.; Robina, Inmaculada; Moreno-Clavijo, Elena; Moreno-Vargas, Antonio J.; Goti, Andrea (2013)
    Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B
    in European journal of organic chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Martella, Daniele; Cardona, Francesca; Parmeggiani, Camilla; Franco, Francisco; Tamayo, Juan A.; Robina, Inmaculada; Moreno-Clavijo, Elena; Moreno-Vargas, Antonio J.; Goti, Andrea (literal)
Pagina inizio
  • 4047 (literal)
Pagina fine
  • 4056 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84879207882&partnerID=q2rCbXpz (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 19 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica Ugo Schiff, Università di Firenze, Polo Scientifico e Tecnologico, Via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy; Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Campus de la Cartuja S/n., 18071 Granada, Spain; CNR-INO and European Laboratory for Non-Linear Spectroscopy (LENS), University of Florence, Via N. Carrara 1, Sesto Fiorentino (FI), Italy; Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/ Prof. García González 1, 41012, Sevilla, Spain (literal)
Titolo
  • Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B (literal)
Abstract
  • The synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B and their biological evaluation as glycosidase inhibitors is reported. The target molecules were obtained through highly stereoselective cycloadditions between sugriched allylic and homoallylic alcohols. This allowed the installation of a methyl group at C5 - a common feature of many natural hyacinthacines - with high control over the stereoselectivity. The new compounds inhibit amyloglucosidase from Aspergillus niger and -glucosidase from almonds. Compound 1 is a competitive inhibitor of amyloglucosidase and shows a fair selectivity towards this enzyme. The presence of C5-Me substitution in indolizidines 2 and 3 slightly diminishes the inhibitory activity towards amyloglucosidase whereas it improves the inhibitory properties towards -glucosidase. (literal)
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