Synthesis of polyacetylene glycosides and thioglycosides

Abstract

Polyacetylene glycosides are natural products isolated from a variety of natural sources, primarily terrestrial plants and fungi. Polyacetylene glycosides isolated to date feature a linear and conjugated polyacetylene chain and a mono di-, or trisaccharide group in their structures. These compounds have been shown to possess a host of different biological activities, including anti-inflammatory effects, inhibition of nitric oxide production and histamine release, anti-bacterial activity, and the ability to inhibit the enzyme 12-lipoxygenase. The project described in this thesis focuses on polyacetylene glycosides and polyacetylene thioglycosides by glycosylating or thioglycosylating mono-, di-, or triyne alcohols, which have been synthesized using the Cadiot-Chodkiewicz reaction and Fritcsh-Buttenberg-Wiechell rearrangement. Twenty-seven polyacetylene glycosides and thioglycosides have been synthesized. Given the structural similarity of these compounds to bioactive natural products, we expected the molecules should have interesting biological activities. Thirty compounds have thus been assayed for cytotoxicity against MCF-7 breast lines, as well as anti-bacterial activity.