Synthesis and evaluation of diorganotin(IV) and triorganotin(IV) derivatives of aspirin, paracetamol and metronidazole as antimicrobial agents

Abstract

A large number of organotin complexes are used as pharmaceuticals, pesticides, stabilizers and fire retardants. In an attempt to explore its pharmaceutical profile, new diorganotin (IV) R2SnA2 (R = n-Bu, n-Oct) and triorganotin (IV) R3SnA2 (R= n-Bu) derivatives where A is the anion of 2-acetoxybenzoic acid (Aspirin), N-(4-hydroxyphenyl) acetamide (Paracetamol) and 2-(2-methyl-5-nitroimidazol-1-yl) ethanol (Metronidazole) have been synthesized. The complexes 1-9 were characterized by elemental analysis as well as FTIR, nuclear magnetic resonance (1H, 13C and 119Sn) spectroscopy. On the basis of these spectroscopic studies it is proposed that diorganotin complexes of Paracetamol and Metronidazole having 1:2 stoichiometry, show tetrahedral geometry while the complexes of Aspirin show octahedral arrangement around tin metal ion with bi-dentate nature of carboxylate group. Triorganotin complexes of Aspirin, Paracetamol and Metronidazole having 1:2 stoichiometry show trigonal bipyramidal geometry with monodentate nature of the carboxylate group around the organotin moiety in the complexes of Aspirin. The ligand molecules bound to the Sn atom through carboxyl oxygen atoms in Aspirin and hydroxyl oxygen in Paracetamol and Metronidazole. The anti-fungal activity of complexes 1, 4 and 9 has been determined against Candida albicans. It is observed that the activity increases on complexation and highest antifungal activity has been found for the triorganotin complex of metronidazole. © 2013 Academic Journals Inc.