Literature

Abstract

Four analogs with 3'-O-alkyl groups (9a: CH(3), 9b: C(2)H(5), 9c: C(13)H(27) or 9d: CH(2)Ph) instead of the 3'-O-sulfate anion in salacinol (1), a naturally occurring potent α-glucosidase inhibitor, were synthesized by the coupling reaction of 1,4-dideoxy-1,4-epithio-d-arabinitols (18a and 18b) with appropriate epoxides (10a-10d). These analogs showed equal or considerably higher inhibitory activity against rat small intestinal α-glucosidases than the original sulfate (1), and one of them (9d) was found more potent than currently used α-glucosidase inhibitors as antidiabetics. Thus, introduction of a hydrophobic moiety at the C3' position of this new class of inhibitor was found beneficial for onset of stronger inhibition against these enzymes.

DOI： 10.1016/j.bmcl.2011.02.109

Biological evaluation of 3′-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3′ position in the side chain on the α-glucosidase inhibitory activity

Bioorganic & Medicinal Chemistry Letters 2011.0

Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’

Bioorganic & Medicinal Chemistry 2016.0

Elongation of the side chain by linear alkyl groups increases the potency of salacinol, a potent α-glucosidase inhibitor from the Ayurvedic traditional medicine “Salacia,” against human intestinal maltase

Bioorganic & Medicinal Chemistry Letters 2021.0

Design and Synthesis of Sulfonium Derivatives: A Novel Class of α-Glucosidase Inhibitors with Potent In Vivo Antihyperglycemic Activities

Journal of Medicinal Chemistry 2023.0

Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases

Bioorganic & Medicinal Chemistry 2008.0

Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors