Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents

• Published in: Bioorganic & medicinal chemistry letters Vol. 16; no. 20; pp. 5403 - 5407
• Main Authors: Loginova, Natalia V., Koval’chuk, Tat’yana V., Zheldakova, Rimma A., Osipovich, Nikolai P., Sorokin, Victor L., Polozov, Genrikh I., Ksendzova, Galina A., Glushonok, Gennady K., Chernyavskaya, Anna A., Shadyro, Oleg I.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15-10-2006; Elsevier
• Subjects: Aminophenols - chemistry; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimicrobial activities; Biological and medical sciences; Copper (II) complexes; Copper - chemistry; General aspects; In Vitro Techniques; Medical sciences; Microbial Sensitivity Tests; Molecular Conformation; Molecular Structure; Organometallic Compounds - chemical synthesis; Organometallic Compounds - chemistry; Organometallic Compounds - pharmacology; Pharmacology. Drug treatments; Sterically hindered o-aminophenols; Structure-Activity Relationship; Copper (II) complexes; Sterically hindered o-aminophenols; Antimicrobial activities; Molecular rigidity; Divalent metal Complexes; Yeast; Ligand; Steric hindrance; Transition metal Complexes; In vitro; Biological activity; Aminophenols; Antimicrobial agent; Screening; Bidentate ligand; Gram positive bacteria; Copper II Complexes; Phenols; Mould; Chemical synthesis; Gram negative bacteria
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2006.07.065

Cu(II) complexes with two sterically hindered
o-aminophenol derivatives have been synthesized and characterized by means of elemental analysis and various physico-chemical techniques. The antimicrobial activities of compounds were tested.
Cu(II) complexes with 4,6-di(
tert-butyl)-2-aminophenol (
I) and 2-anilino-4,6-di(
tert-butyl)phenol (
II) have been synthesized and characterized by means of elemental analysis, TG/DTA, FT-IR, UV–vis, ESR, and conductance measurements. The compounds
I and
II can coordinate in their singly deprotonated forms and behave as bidentate O,N-coordinated ligands; their CuL
2 complexes are characterized by CuN
2O
2 coordination modes and square planar geometry. In vitro antimicrobial screening against Gram-positive and Gram-negative bacteria, yeasts, and moulds indicated that the compound
I and its Cu(II) complex were more active than Questiomycin B, the compound
II, and its Cu(II) complex.