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Updated: Jul 19, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity
Ying Shao1, Muraoka Osamu, Yoshikai Kazuya
1Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China. shaoy@cde.org.cn
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 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.
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.
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