187590-77-8Relevant articles and documents
A new class of glycosidase inhibitor: Synthesis of salacinol and its stereoisomerst
Ghavami,Johnston,Pinto
, p. 2312 - 2317 (2001)
Salacinol (4) 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 syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitol at C-1 of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate. The work serves to resolve the ambiguity about the exact structure of salacinol and establishes conclusively the structure of the natural product.
COMPOUNDS USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE SAME, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP
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, (2018/02/28)
PROBLEM TO BE SOLVED: To provide novel compounds useful for manufacturing salacinol, a method for manufacturing the compounds, a method for manufacturing salacinol, methods for protecting and deprotecting a diol group, and a protective agent for a diol group. SOLUTION: A compound represented by formula (7a) is a compound useful for manufacturing salacinol. (In the formula, R4ba is a p-toluoyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the α-glucosidase inhibitory activity
Tanabe, Genzoh,Yoshikai, Kazuya,Hatanaka, Takanori,Yamamoto, Mizuho,Shao, Ying,Minematsu, Toshie,Muraoka, Osamu,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 3926 - 3937 (2008/02/13)
De-O-sulfonated analogs (10a, Y- = CH3OSO3 and 10b, Y- = Cl) of salacinol, a naturally occurring glycosidase inhibitor, and its diastereomer (12a, Y- = CH3OSO3) with l-thiosugar moiety (1,4-dideoxy-1,4-epithio-l-arabinitol) were prepared. Their inhibitory activities against intestinal maltase and sucrase were examined and compared with those of the parent α-glycosidase inhibitor, salacinol (1a). Compounds 10a and 10b showed a potent inhibitory activity equal to that of 1a against both enzymes, although 12a was a weak inhibitor against sucrase and maltase. These results indicated that the O-sulfonate anion moiety of 1a is not essential for the inhibitory activity.