Specific, uncompetitive inhibition of β-galactosidases by a 5,6-isopropylidenedioxyfuro[2,3-d]isoxazole-3-methanol derivative

Synthesis of a 5-Hydroxypiperidine-2,3,4,6-tetramethanol, a New 2,6-Dideoxy-2,6-iminoheptitol Derivative

“…Inhibitors of glycohydrolases do not have to be transition state mimetics of the enzyme-catalyzed hydrolysis of the glycosidic bond . Compound that do not resemble sugars such as (−)-(3a S ,5 S ,6 S ,6a R )-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro[2,3- d ]isoxazole-3-methanol inhibits β-galactosidase from Aspergillus niger ( K i = 18 μM) and that from Aspergillus orizae ( K i = 72 μM) specifically (uncompetitive inhibition) . The neutral C-disaccharide α-C(1→3)-mannopyranoside of N -acetylgalactosamine is a inhibitor of β-galactosidase from jack bean ( K i = 7.5 μM, mixed mode of inhibition) …”

“…We report here the synthesis of 1, a new kind of hydroxymethylated piperidine, starting from rac-2, an inexpensive Diels-Alder adduct of maleic anhydride to furfuryl alcohol. Reduction of 2 with LiAlH 4 gave triol 3 [7][8][9][10][11] which was peracetylated into triacetate 4. 12 Treatment of 4 with BBr 3 at -78 °C provided the allylic bromide 5 (95%) that could be displaced by tetramethylguanidinium azide to produce the corresponding azido derivative 6 (93% yield).…”

New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards α-glucosidase

“…[14][15][16] However, most of developed glycosidase inhibitors are sugar mimics which require tedious multi-steps chemical procedures. [17][18][19] Amongst the various types of glucosidase inhibitors, also non-sugar derivatives have drawn considerable attention. Indeed, there is great structural diversity amongst glucosidase inhibitors, which are not based on a sugar scaffold.…”

A One-Pot Approach to Δ2-Isoxazolines from Ketones and Arylacetylenes

“…The Δ 2 -isoxazoline structural unit is a frequently met active pharmacophore in numerous biologically important molecules including those possessing antifungal, antibacterial, antitubercular, siderophore, antidepressant, and β-galactosidase inhibiting properties . Some of them exhibit promising antiviral activity, e.g.…”