Synthesis of polyfunctional quinolizidine alkaloids: development towards selective glycosidase inhibitors

A highly divergent route to a variety of quinolizidine alkaloids is described. The enantiomeric precursors and utilized for the synthesis of these alkaloids were constructed stereospecifically from the PET cyclization of the corresponding acetylene tethered alpha-trimethylsilyl amine moieties and ,...

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Veröffentlicht in:Organic & biomolecular chemistry 2009-01, Vol.7 (16), p.3300-3307
Hauptverfasser: Pandey, Ganesh, Grahacharya, Debasish, Shashidhara, K S, Khan, M Islam, Puranik, Vedavati G
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Sprache:eng
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Zusammenfassung:A highly divergent route to a variety of quinolizidine alkaloids is described. The enantiomeric precursors and utilized for the synthesis of these alkaloids were constructed stereospecifically from the PET cyclization of the corresponding acetylene tethered alpha-trimethylsilyl amine moieties and , respectively, both of which were synthesised from D-ribose. The polyhydroxy quinolizidine alkaloid was found to be a selective inhibitor of alpha-galactosidase with Ki 83.9 microM. The amine analogs , and are found to be selective and potent inhibitors of alpha-glucosidase with Ki 28, 120 and 140 microM, respectively.
ISSN:1477-0520
1477-0539
DOI:10.1039/b907007a