Polycyclitols: novel conduritol and carbasugar hybrids as new glycosidase inhibitors

Mehta, Goverdhan ; Ramesh, Senaiar S. (2005) Polycyclitols: novel conduritol and carbasugar hybrids as new glycosidase inhibitors Canadian Journal of Chemistry, 83 (6-7). pp. 581-594. ISSN 0008-4042

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Official URL: http://rparticle.web-p.cisti.nrc.ca/rparticle/Abst...

Related URL: http://dx.doi.org/10.1139/v05-032

Abstract

A family of novel carbasugar analogues (bicyclitols) based on cis-hydrindane and cis-decalin frameworks has been conceptualized. These novel entities can be regarded as conduritol and carbasugar hybrids. Syntheses of these polyhydroxylated entities have been achieved in stereo- and regioselective manners, starting from the readily available Diels-Alder adducts of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and appropriate dienophiles like cyclopentadiene or p-benzoquinone, that embody a masked 7-ketonorbornenone moiety. Thermally induced chelotropic elimination of CO from the appropriately functionalized 7-ketonorbornenone derivatives to deliver annulated bicyclic 1,3-cyclohexadiene derivatives was the key step in this synthetic endeavor. Further oxy-functionalization of the 1,3-cyclohexadiene moiety delivered the targeted polycyclitols. A preliminary investigation of the glycosidase inhibitory potency of these bicyclitols, identified compounds 18 and 54 as potent and selective inhibitors of α-glucosidase (yeast).

Item Type:Article
Source:Copyright of this article belongs to Canada Institute for Scientific and Technical Information.
Keywords:Carbasugar; Conduritol; Glycomimics; Glycosidase Inhibitors
ID Code:29012
Deposited On:18 Dec 2010 05:42
Last Modified:18 Dec 2010 05:42

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