347362-39-4Relevant academic research and scientific papers
Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors
Johnston, Blair D.,Ghavami, Ahmad,Jensen, Morten T.,Svensson, Birte,Pinto, B. Mario
, p. 8245 - 8250 (2002)
The syntheses of two selenium analogues (10 and 11) of the naturally occurring sulfonium ion, salacinol (3), are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The synthetic strategy relies on the nucleophilic attack of a 2,3,5-tri-O-benzyl-1,4-anhydro-4-seleno-D-arabinitol at the least hindered carbon of benzyl- or benzylidene-protected D- or L-erythritol-1,3-cyclic sulfate. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as a solvent in the coupling reaction proves to be beneficial. Enzyme inhibition assays indicate that 10 is a better inhibitor (Ki = 0.72 mM) of glucoamylase than 3, which has a Ki value of 1.7 mM. In contrast, 11 showed no significant inhibition of glucoamylase. Compounds 10 and 11 showed no significant inhibition of barley-α-amylase or porcine pancreatic-α-amylase.
Glycosidase inhibitors and methods of synthesizing same
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, (2008/06/13)
A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes c
Glycosidase inhibitors and methods of synthesizing same
-
, (2008/06/13)
A method for synthesizing Salacinol, its stereoisomers, and non-naturally occurring selenium and nitrogen analogues thereof having the general formula (I): The compounds are potentially useful as glycosidase inhibitors. The synthetic schemes comprise reac
