Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 12, Pages 4580-4586Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05324h
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Funding
- Korea government (MEST) [R32-2008-000-10098-0, NRF-C1ABA001-2010-0020428]
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Based on the structures of natural sphingolipids, we designed heterocyclic sphingoid base mimetics in which the conformational restriction is introduced by incorporation of a pyrrolidine moiety between the 2-amino group and the C-4 carbon atom of the sphingoid base. Our synthesis features a regioselective nucleophilic ring opening of a cyclic sulfate with cyanide and subsequent manipulation of the cyanide group. During the course of synthesis, Staudinger-type reductive cyclization of 1,3-azido carboxylic acid and 1,4-azido alcohol offers a direct route to the five-membered pyrrolidone and pyrrolidine products. The preliminary biological evaluation indicates that the designed pyrrolidine analog is biologically active and its cytotoxic effect is associated with the induction of apoptosis.
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