Synthesis of heterocyclic analogs of amino acids and peptides

Functionalised heterocyclic compounds containing an amino acid or a peptide structural element represent an important group of organic compounds (peptidomimetics) with potential biological activity. Witihin the frame of the proposed research project, novel reagents and synthetic methodologies for the preparation of heterocyclic analogs of amino acids and peptides, as well as related functionalised heterocyclic compounds, will be developped. The main issues of this research project are: a) development of new general synthetic methodologies and new reagents, which would enable selective preparation of diverse types of peptidomimetics (selectivity and diversity oriented synthesis) b) stereochemical studies directed towards development of stereoselective synthetic methods c) application of new reagents and new synthetic methosdologies in parallel and combinatorial synthesis. Within the frame of the above mentioned general research orientation, the following topics will be studied: a) preparation and synthetic applications of new chiral enaminones in the synthesis of optically active heteroarylalanines and related compounds, synthesis of heterocyclic systems with incorporated amino acid structural element, and synthesis of natural product analogs b) study on reactivity of enaminones towards organometallic reagents followed by applications in the synthesis of dehydroalanines, analogs of aplysinopsins, and related compounds c) study on regio- and stereoselective 1,3-dipolar cycloadditions 3-pyrazolidinone-1-azomethine imines leading to 2-amino-1-oxopyrazolo(1,2-a)pyrazole-7-carboxylates as heterocyclic analogs of dipeptides e) applications of new synthetic methods and new reagents in solid-phase synthesis of functionalised heterocycles.