Synthesis and applications of novel nitrogen heterocycles

Abstract

Pyridines and triazines are nitrogen heterocycles found in all fields of the chemical realm. These aromatic compounds readily undergo nucleophilic aromatic substitution reactions. Nitrogen heterocycles appear in therapeutics, reactive dyes, herbicides, catalysts, and others. Exploration of pyridines and triazines in our laboratory, resulted in novel compounds with potential applications. A triazine ligand was developed containing pyrazolone and hydrazine groups, capable of binding to first row transition metals. Copper (II), nickel (II), and zinc (II) formed chelates through a unique 6,5 oxygen to metal binding ring systems. The chelating ability of this ligand led to promising results in its antioxidant ability, and cellular toxicity. (Chapter 1). Homo- and heterodimeric peptide macrocycles were synthesized and characterized. The facile route for the preparation of these compounds enable for rapid and selective transformations of diverse dimeric macrocycles. Analysis via mass spectrometry, NMR spectroscopy, and X-ray diffractometry determined the formation of 24-membered macrocycles. Glycine, and Lphenylalanine amino acid residues were incorporated into the macrocycles as well as substituted hydrazines as amino acid side chain mimics. These compounds find potential applications in a broad field of biological sciences. (Chapter 2). Finally, four members of a class of pyridine containing macrocycles bearing electron withdrawing groups in the 4-position (CN, NO2, Cl, CF3), were synthesized as targets for metal chelation and catalysis. (Chapter 3).