Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity.
- Author:
Ying SHAO
1
;
Muraoka OSAMU
;
Yoshikai KAZUYA
;
Matsuura YOSHIHARU
;
Yamada ERIKO
;
Minematsu TOSHIE
;
Tanabe GENZOH
;
Matsuda HISASHI
;
Yoshikawa MASAYUKI
;
Qi-dong YOU
Author Information
- Publication Type:Journal Article
- MeSH: Animals; Enzyme Inhibitors; chemical synthesis; chemistry; pharmacology; Glycoside Hydrolase Inhibitors; Intestinal Mucosa; drug effects; enzymology; Molecular Structure; Nitrogen Compounds; chemical synthesis; pharmacology; Rats; Structure-Activity Relationship; Sugar Alcohols; chemical synthesis; chemistry; pharmacology; Sulfates; chemical synthesis; chemistry; pharmacology; alpha-Glucosidases; metabolism
- From: Acta Pharmaceutica Sinica 2006;41(7):647-653
- CountryChina
- Language:English
-
Abstract:
AIMTo investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents.
METHODSThe synthesis of the key intermediate 2, 4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from D-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal alpha-glucosidase in vitro and compared with that of salacinol.
RESULTSA nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b.
CONCLUSIONSubstitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
