Synthesis of carbohydrate derivatives with biological activities

In this work the objective was to synthesize new molecules with potential biological activity. Among the synthesized compounds, C-nucleosides, azidosugars, iminosugars and triazoles stand out. C-nucleosides were synthesized through a precursor derived from glucosamine HCl. Glucosamine HCl was transformed in two different aldehydes, which by Biginelli reaction originated a new heterocyclic ring connected to a carbohydrate through a carbon-carbon bond. Through this method was possible to obtain oxopyrimidines and thioxopyrimidines attached to carbohydrate. Simple azidosugars derived from commercial carbohydrates where synthesized. The synthesis of these azido-sugars may be found in literature. The obtained yields were similar to the ones found in literature. The scope of this synthesis was the application of azido-sugars as triazol precursors, i.e., its application in Click Chemistry reaction. Azido-sugars were also fused with the 1,3-oxazolidine-2-thione, 1,3-oxazolidin-2-one and 2- benzylsulfanil-1,3-oxazoline ring. This way a new methodology was developed for synthesis of these innovative structures. Iminosugars fused with an 1,3-oxazolidin-2-one ring were synthesized. A new methodology using azidosugars precursors fused with 1,3-oxazolidin-2-ones was developed. Alkynyl-lactams were prepared starting from azidolactams already described in literature. Applying “Click Chemistry” triazoles where synthesized, using as precursors the azides and alkynyl lactams previously synthesized. The biological activity of some compounds was tested. The ability to inhibit the growth of Rhipicephalus (Boophilus) microplus and consequently the oviposition (laying eggs). The ability of some molecules was tested for inhibiting glycosidases. Cell viability was determined for some molecules. Some compounds showed promising activities