Analogues of Moranoline and Mdl 73945. Methyl 6(5)-Deoxy-6(5)-(Morpholin-4-Yl)-α-D-Glycosides as Glucosidase Inhibitors
Titel:
Analogues of Moranoline and Mdl 73945. Methyl 6(5)-Deoxy-6(5)-(Morpholin-4-Yl)-α-D-Glycosides as Glucosidase Inhibitors
Auteur:
Ashry, El Sayed H. El Abdel-Rahman, Adel A. -H. Kattab, Mohamed Shobier, Aida H. Schmidt, Richard R.
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 19 (2000) nr. 3 pagina's 345-357
Jaar:
2000
Inhoud:
Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6), or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of β-D-glucosidase from sweet almond and using o-nitrophenyl β-D-glucopyranoside as substrate exhibited a Ki value for 21 on the same order as 1-deoxynojirimycin whereas for 3, a Ki value of lesser order was observed.