Synthesis and characterization of alkaloid derived hydrazones and their metal (II) complexes

Abstract

Alkaloids have been known overtime to have medicinal uses. Exploring alkaloid derived hydrazones and their complexes as potential therapeutic agents with a view to improving the medicinal uses of alkaloids are imperative. 1,8-dichloroacridone hydrazone hydrochloride, 1-chloro pilocarpine nitrate-3-chlorophenyl hydrazone and 1-phenethyl-4-piperidone formyl hydrazone ligands were synthesized via Wolff–Kishner condensation reaction. Five metal (II) complexes of cobalt, nickel and manganese were prepared by stirring the ligands with the respective metal salts. The ligands and complexes were characterized using elemental analyses, molar conductivity, FTIR, 1H and 13C nmr, UV–Vis spectra, melting point and solubility. Antimicrobial activities of the ligands and their complexes were tested against four bacteria (Staphylococcus aureus, Streptococcus faecalis Escherichia coli, Salmonella paratyphimurium) and a fungus (Candida albican). The molar conductance values indicate that they are 1:1 and 1:2 type electrolytes while the elemental analyses of the complexes reveals a 1:1 metal to ligand stoichiometry. The relevant IR bands suggest coordination is through the C=N, C=O, N=C–O and C–N groups. Both 1H and 13C nmr corroborated the elemental analysis while the UV–Vis reveals intra-ligand charge transfer while the complexes exhibited the expected metal transitions bands. A proposed octahedral geometry is supported by spectral data. Only 1, 8-dichloroacridonehydrazone hydrochloride ligand was found to be active against all the organisms. Cobalt and nickel complexes of 1,8-dichloroacridonehydrazone hydrochloride were active against S. paratyphimurium and S. aureus, respectively, while cobalt complex of 1-chloropilocarpinenitrate-3-chlorophenylhydrazone was active against S. faecalis and S. paratyphimurium. The minimum inhibitory concentrations (MIC) were also recorded.