Synthesis, characterization, and antifungal studies of transition metal complexes of ω-bromoacetoacetanilide isonicotinylhydrazone

• Published in: Applied biochemistry and biotechnology 2004-07, Vol.118 (1-3), p.283-292
• Main Authors: DEEPA, K. P, ARAVINDAKSHAN, K. K
• Format: Article
• Language: English
• Subjects: Acetoacetanilides; Anions; Antibacterial agents; Anticancer properties; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antiinfectives and antibacterials; Antitumor activity; Biological and medical sciences; Biotechnology; Catalysts; Cell walls; Chelates; Chelating agents; Coordination compounds; Diketones; Fundamental and applied biological sciences. Psychology; Fungi; Fungi - drug effects; Fungicides; Infrared analysis; Isoniazid; Isoniazid - analogs & derivatives; Isoniazid - chemical synthesis; Isoniazid - chemistry; Isoniazid - pharmacology; Ligands; Magnetic Resonance Spectroscopy; Magnetics; Metal complexes; Metal ions; Microorganisms; NMR; Nuclear magnetic resonance; Pigments; Spectrophotometry, Infrared; Synthesis; Transition Elements - chemistry; Transition Elements - pharmacology; Transition metal compounds; Tuberculosis
• ISSN: 0273-2289; 1559-0291; 0273-2289
• DOI: 10.1385/ABAB:118:1-3:283

Isonicotinic acid hydrazide or isonicotinylhydrazide, commonly known as isoniazid, is an antibacterial agent that has been used to treat tuberculosis. It interacts with microbial cell walls. Schiff's bases or anils are the compounds having >C=N-N< linkages, which have immense applications as catalysts, stabilizers, pigments, dyes, and drugs. They have good ability to form chelates with many metal ions. Isoniazid can form Schiff's bases with diketones such as acetoacetanilide. Acetoacetanilide isonicotinylhydrazone and its metal chelates exhibit anticancer activity. Our studies on N-methylacetoacetanilide isonicotinylhydrazone and its metal chelates revealed that they are active against pathogenic fungal strains. Hence, it is worthwhile to synthesize new complexes of ligands having different substituents on the acetoacetanilide moiety. We synthesized five new metal chelates of omega-bromoacetoacetanilide isonicotinylhydrazone. The ligand behaved as a tridentate monoanion or as a tridentate dianion in the complexes. These compounds were characterized mainly by elemental analysis; conductivity measurements; and electronic, infrared, and nuclear magnetic resonance spectral studies. We also carried out antifungal studies of these compounds against four selected pathogenic fungal strains using a cup-plate technique. Both the ligand and its metal chelates were active against all fungal strains investigated. However, the chelates were found to be more active than the ligand.