Study of some carbazones and hydrazones: synthesis, characterization and pharmaceutical properties

Abstract

Hydrazones and their derivatives are very important compounds in medicinal chemistry due to their reported biological activity for the treatment of several diseases. Among biological properties of this class of compounds, antimicrobial activity is the most frequently encountered in scientific literature. They are also important intermediates in organic synthesis. In this research, we have studied and compared the antiparasitic activity of four hydrazone derivatives. These were 4-phenyl-3-thiosemicarbazone and the p-tosylhydrazone of 4'-methylacetophenone (1, 2) and S-(+)-carvone (3, 4) respectively. Their structure was characterized by spectrometrical analysis (TLC, IR, NMR 1H & 13C and ESI‐MS) and then, their antiparasitic activity was evaluated on Trypanosoma brucei brucei and toxicity against Artemi a salina Leach. All the products were obtained in good yields (59-90%) and high purity, showing high stability, according to spectral analyses. Among the molecules, only p-tosylhydrazone of S-(+)-carvone (4) exhibited a moderate trypanocidal activity (half-inhibitory concentration IC50 = 27.75 ± 3.47 micromolar). It was found non-toxic on the larvae and proved to be fairly selective on the parasite, with a good selectivity index (SI = 18 >> 1). This study could open other fields of research on hydrazones they have advantageous properties compatible with the reasonable pharmacokinetics and drug availability.