Peracetylated carbohydrates have been used previously as glycoconjugates to aid membrane permeability of small drug-like molecules. In addition, there has been much work carried out to modify and improve current drugs via conjugation to amino acids and peptides.Non-steroidal anti-inflammatory drugs (NSAIDs) are a class of compound used for the management of pain, in particular as a treatment for osteo- and rheumatoid arthritis. The chronic use of NSAIDs is associated, however, with adverse side effects, many related to the gastrointestinal tract. There is also an increased risk of coronary heart disease and heart failure.Glucosamine supplements are available to the public as an alternative treatment for the symptoms of osteoarthritis and there are no adverse effects associated with this supplement. We envisaged therefore, that glucosamine could be modified by reaction with an activated NSAID via an amino acid linker to develop a series of novel glucosamine-NSAID conjugates.We describe herein synthetic studies to access glucosamine-NSAID conjugates and subsequent applications of this chemistry in the synthesis of carbohydrate-antibiotic conjugates.

Synthesis of carbohydrate-drug conjugates: Potential NSAID pro-drugs

248th National Meeting (2014)

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