Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity
- VernacularTitle:一种新的合成salacinol衍生物的方法及其对α-糖苷酶的抑制活性
- Author:
Ying SHAO
;
Muraoka OSAMU
;
Yoshikai KAZUYA
;
Matsuura YOSHIHARU
;
Yamada ERIKO
;
Minematsu TOSHIE
;
Tanabe GENZOH
;
Matsuda HISASHI
;
Yoshikawa MASAYUKI
;
Qidong YOU
- Publication Type:Journal Article
- Keywords:
synthesis;
cyclic sulfate;
erythritol;
salacinol;
glycosidase inhibitor;
glucosidase inhibitor;
azasugar
- From:
Acta Pharmaceutica Sinica
2006;41(7):647-653
- CountryChina
- Language:Chinese
-
Abstract:
Aim To investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. Methods The synthesis of the key intermediate 2,4-O-isopropylidene-L-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from Dglucose 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 α-glucosidase in vitro and compared with that of salacinol. Results A nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. Conclusion Substitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.
