872976-89-1Relevant academic research and scientific papers
Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives
Lysek, Robert,Schuetz, Catherine,Favre, Sylvain,O'Sullivan, Anthony C.,Pillonel, Christian,Kruelle, Thomas,Jung, Pierre M.J.,Clotet-Codina, Imma,Este, Jose A.,Vogel, Pierre
, p. 6255 - 6282 (2007/10/03)
A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (±)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward α-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.
(1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation
Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
, p. 2788 - 2811 (2007/10/03)
(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases
Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors
Lysek, Robert,Schuetz, Catherine,Vogel, Pierre
, p. 3071 - 3075 (2007/10/03)
The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)3.
