Some 1,4-morpholin-2,5-dione derivatives have been synthesized in good yields by a procedure already employed by us starting from (S)- phenylethylamine, ethylbromoacetate and 2 chloropropionyl chloride. Both (6S)- and (6R)-6-methy-1,4-morpholin-2,5 diones were alkylated with allylbromide, then converted into epoxiderivatives and finally hydrolised to the vicinal diols. The absolute configuration of the C-2’ stereocenter in the epoxides, and then in the diols, was established by the conversion of the diols into the respective gamma-lactones. Except the allylderivatives which show a weak biological activity (Ki=1300 and 3300 micromolar), both epoxides and diols are non competitive inhibitors towards the alpha-glucosidase from bakers yeast (Ki values between 47-470 micromolar). No significant inhibitory effect towards both beta-glucosidase (from almonds) and alpha-mannosidase (from jack beans) was observed.

Chiral 1,4-morpholine-2,5-dione derivatives as alpha-glucosidase inhibitors

ARCELLI, ANTONIO;PORZI, GIANNI;SANDRI, SERGIO
2004

Abstract

Some 1,4-morpholin-2,5-dione derivatives have been synthesized in good yields by a procedure already employed by us starting from (S)- phenylethylamine, ethylbromoacetate and 2 chloropropionyl chloride. Both (6S)- and (6R)-6-methy-1,4-morpholin-2,5 diones were alkylated with allylbromide, then converted into epoxiderivatives and finally hydrolised to the vicinal diols. The absolute configuration of the C-2’ stereocenter in the epoxides, and then in the diols, was established by the conversion of the diols into the respective gamma-lactones. Except the allylderivatives which show a weak biological activity (Ki=1300 and 3300 micromolar), both epoxides and diols are non competitive inhibitors towards the alpha-glucosidase from bakers yeast (Ki values between 47-470 micromolar). No significant inhibitory effect towards both beta-glucosidase (from almonds) and alpha-mannosidase (from jack beans) was observed.
V° International Congress Chemistry and Chemical Engineering
169
169
A. Arcelli; A. Grandi; G. Porzi; S. Sandri
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/11222
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