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Synthesis of a new series of alpha‐(N)‐heterocyclic thiosemicarbazone ligands and their Cu 2+ , Pd 2+ , and Pt 2+ metal complexes: Differences in Biological Activity
Author(s) -
Rand Victoria Grace,
Lisic Edward
Publication year - 2016
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.30.1_supplement.612.15
Subject(s) - semicarbazone , ribonucleotide reductase , chemistry , stereochemistry , metal , ligand (biochemistry) , group 2 organometallic chemistry , combinatorial chemistry , medicinal chemistry , molecule , organic chemistry , biochemistry , receptor , protein subunit , gene
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 a series of new alpha‐(N)‐heterocyclic thiosemicarbazone ligands based on 2‐propionylthiazole. To this substrate, seven different thiosemicarbazides were attached to form the thiosemicarbazones reported here. These 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 Cu 2+ , Pt 2+ , and Pd 2+ 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.