1310460-66-2

Upstream product

• 100-39-0 benzyl bromide 
• 1310460-63-9 1-O-benzyl-2-O-methyl-D-erythritol 
• 1310460-60-6 1-O-benzyl-2-O-methyl-3,4-O-isopropylidene-D-erythritol 
• 1310460-70-8 (1S)-2-(benzyloxy)-1-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol 

Downstream Products

• 1310460-59-3 2,3,5-tri-O-benzyl-1,4-[(R)-[1-O-benzyl-4-deoxy-2-O-methyl-D-erythritol-4-yl]episulfoniumylidene]-1,4-dideoxy-D-arabitol chloride 

Relevant academic research and scientific papers

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

Using an in silico method, seven analogs bearing hydrophobic substituents (8a: Me, 8b: Et, 8c: n-Pent, 8d: n-Hept, 8e: n-Tridec, 8f: isoBu and 8g: neoPent) at the 3′-O-position in salacinol (1), a highly potent natural α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’, were designed and synthesized. In order to verify the computational SAR assessments, their α-glucosidase inhibitory activities were evaluated in vitro. All analogs (8a–8g) exhibited an equal or considerably higher level of inhibitory activity against rat small intestinal α-glucosidases compared with the original sulfonate (1), and were as potent as or higher in potency than the clinically used anti-diabetics, voglibose, acarbose or miglitol. Their activities against human maltase exhibited good relationships to the results obtained with enzymes of rat origin. Among the designed compounds, the one with a 3′-O-neopentyl moiety (8g) was most potent, with an approximately ten fold increase in activity against human maltase compared to 1.

CYCLIC SULFONIUM SALT, PROCESS FOR PRODUCTION OF SAME, AND alpha-GLUCOSIDASE INHIBITOR COMPRISING SAME

Provided is a novel cyclic sulfonium salt compound which is useful for the prevention or treatment of diabetes and the like. The present invention relates to a novel cyclic sulfonium salt compound represented by general formula (I) or (II), an isomer or solvate of the compound, or a pharmaceutically acceptable salt of the compound or the isomer or solvate. The present invention also relates to an α-glucosidase inhibitor, a pharmaceutical composition for preventing or treating diabetes, and an anti-diabetes food, each of which comprises the compound represented by general formula (I) or (II) and the like.

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

Four analogs with 3′-O-alkyl groups (9a: CH3, 9b: C 2H5, 9c: C13H27 or 9d: CH 2Ph) 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.