Abstract
Thiosemicarbazones (TSCNs) constitute a broad family of compounds (R1R2C=N-NH-C(S)-
NR3R4), particularly attractive because many of them display some biological activity against a wide
range of microorganisms and cancer cells. Their activity can be related to their electronic and structural
properties, which offer a rich set of donor atoms for metal coordination and a high electronic delocalization
providing different binding modes for biomolecules. Heterocycles such as pyrrole, imidazole and
triazole are present in biological molecules such as Vitamine B12 and amino acids and could potentially
target multiple biological processes. Considering this, we have explored the chemistry and biological
properties of thiosemicarbazones series and their complexes bearing heterocycles such as pyrrole, imidazole,
thiazole and triazole. We focus at the chemistry and cytotoxicity of those derivatives to find out
the structure activity relationships, and particularly we analyzed those examples with the TSCN units in
which the mechanism of action information has been profoundly studied and pathways determined, to
promote future studies for heterocycle derivatives.
Keywords:
Biological-activity, Coordination, Heterocycles, Metallodrugs, Structure-activity relationship, Thiosemicarbazones.
Graphical Abstract
[2]
Siddiqui, E.J.; Azad, I.; Khan, A.R.; Khan, T. Thiosemicarbazone Complexes as versatile medicinal chemistry agents: A Review. J. Drug Deliv. Ther., 2019, 9(3), 689-703.
[21]
Li, X-J.; Mao, P-D.; Wu, W-N.; Kou, K.; Liu, S-Y.; Wang, Y. Ni/Cu complexes with two pyrrole thiosemicarbazone ligands: crystal structures and dna interaction. Wuji Huaxue Xuebao, 2017, 33(7), 1257-1265.
[24]
Sen, S.K.; Assefa, A.G. Synthesis, characterization and antimicrobial studies of oxo vanadium (iv & v) complexes with semi and thiosemicarbazones of furan-2-carbaldehyde and pyrrole-2-carbaldehyde. Chem. Sci. Int. J., 2015, 7(4), 227-235.
[56]
Lo Meo, P.; Gruttadauria, M.; Noto, R. Oxidative cyclization of aldehyde thiosemicarbazones induced by potassium ferricyanide and by tris(p-bromophenyl)amino hexachloroantimoniate. A joint experimental and computational study (05-1281CP). ARKIVOC, 2005, 2005(1), 114-129.
[71]
Verbeek, J.; Eriksson, J.; Syvenen, S.; Huisman, M.; Schuit, R. C.; Molthoff, C. F. M.; Voskuyl, R. A.; de Lange, E. C.; Lammertsma, A. A.; Windhorst, A. D. Synthesis and preliminary preclinical evaluation of fluorine-18 labelled isatin-4-(4-methoxyphenyl)-3-thiosemicarbazone ([18-F] 4FIMPTC) as a novel PET tracer of Pglycoprotein expression. EJNMMI radiopharmacy and chemistry, 2018, 3(1), 11.