Triapine®, which has recently made it to stage II clinical trials as an anticancer agent, and other similar alpha-(N)-heterocyclic thiosemicarbazone ligands act as ribonucleotide reductase poisons. Copper complexes of these same ligands also inhibit cell replication by an entirely different mechanism, attacking Topoisomerase IIα. The focus of this research is on synthesis and characterization of three series of new alpha-(N)-heterocyclic thiosemicarbazone ligands based on thiazole-2-carboxaldehyde, 2-acetylthiazole, and 2-acetyl-4-methylthiazole. To these three substrates, seven different thiosemicarbazides were attached to form the thiosemicarbazones reported here. These 21 new thiosemicarbazone ligands were then characterized by NMR, melting point, and MS. Once characterized and purified, these mono-anionic tridentate ligands were then reacted with Cu2+ and Pd2+ to make the square planar metal complexes. These were again characterized by UV/Vis, melting point, MS, and NMR, where applicable. All of the metal complexes and ligands were tested with Minimum Inhibitory Concentration (MIC) studies using seven different microbes to test their potency. As will be shown, many of the new compounds exhibit profound anti-microbial properties.

Synthesis, NMR characterization, and MIC studies of a new series of alpha-(N)-heterocyclic thiosemicarbazone ligands and their Pd2+ and Cu2+ metal complexes

249th National Meeting (2015)

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