Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1390539 | Carbohydrate Research | 2011 | 8 Pages |
Abstract
An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from d-(â)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against β-galactosidase (IC50 = 3 μM). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities.
Related Topics
Physical Sciences and Engineering
Chemistry
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Authors
Tzenge-Lien Shih, Ming-Tsung Liang, Kuen-Da Wu, Chun-Hung Lin,