Mane, Rajendra S. ; Ghosh, Sougata ; Singh, Shailza ; Chopade, Balu A. ; Dhavale, Dilip D. (2011) Synthesis of anomeric 1,5-anhydrosugars as conformationally locked selective α-mannosidase inhibitors Bioorganic & Medicinal Chemistry, 19 (22). pp. 6720-6725. ISSN 0968-0896
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.bmc.2011.09.046
Abstract
Anomeric 1,5-anhydrosugar 2 was synthesized from D-glucose derived N-Cbz protected aminodiol 8. The key step involves, acid catalyzed hydrolysis of 1,2-acetonide group in 8 to get hemiacetal that concomitantly undergoes formation of the pyranose ring by attack of C-3 hydroxyethyl group on anomeric C-1, leading to the formation of dioxabicyclo[3.2.1]octane skeleton which on hydrogenolyis gave 2. The glycosidase inhibitory activities of hydroxy- and amino-substituted anomeric 1,5-anhydrosugars 1 and 2, respectively, showed selective inhibition of α-mannosidase. These results were substantiated by molecular docking studies using WHAT IF software and AUTODOCK 4.0 program.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Anomeric Anhydrosugars; α-Mannosidase Inhibitors; D-Glucose |
| ID Code: | 87221 |
| Deposited On: | 16 Mar 2012 06:16 |
| Last Modified: | 19 Mar 2012 11:34 |
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