Synthesis of polyhydroxy piperidines and their analogues: a novel approach towards selective inhibitors of alpha-glucosidase |
| |
Authors: | Pandey Ganesh Bharadwaj Kishor Chandra Khan M Islam Shashidhara K S Puranik Vedavati G |
| |
Affiliation: | Organic Chemistry Division, National Chemical Laboratory, Pune-411008, India. gp.pandey@ncl.res.in |
| |
Abstract: | Various polyhydroxy piperidine azasugars have been synthesized from precursors 18a and 18b, obtained in both enantiomeric forms from d-ribose. Out of these polyhydroxy piperidine azasugars, 22, 39 and 20 were found to be potent as well as selective inhibitors of alpha-glucosidase with K(i) values ranging as low as 1.07 microM, 16.4 microM, and 88.2 microM, respectively. Replacement of the hydroxy methylene moiety of (K(i) 33% at 1 mM) by an amino methylene moiety (32, K(i) 36.8 microM) showed a remarkable increase in the activity (almost 30 times). Furthermore, increasing the lipophilicity of by N-alkylation with a dodecyl group (36) showed a three-fold enhancement in the activity (K(i) 217 microM to K(i) 72.3 microM). |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|