Copper complexes with heterocyclic sulfonamides: synthesis, spectroscopic characterization, microbiological and SOD-like activities: crystal structure of [Cu(sulfisoxazole)2(H2O)4] . 2H2O.
The synthesis, characterization and comparative biological study of a series of antibacterial copper complexes with heterocyclic sulfonamides were reported. Two kinds of complexes were obtained with the stoichiometries [Cu(L)2] . H2O and [Cu(L)2(H2O)4] . nH2O. They were characterized by infrared and electronic spectroscopies and the crystal structure of [Cu(sulfisoxazole)2(H2O)4] . 2H2O was determined by single crystal X-ray diffraction. It crystallized in the C2/c with Z = 8 monoclinic space group C2/c with Z = 8. The Cu(II) is in a slightly tetragonal distorted octahedron formed by four oxygen atoms from water molecules and two nitrogen atoms from two isoxazole rings. The antimicrobial activity was evaluated for all the synthesized complexes and ligands using the agar dilution test. The results showed that the complexes with five-membered heterocyclic rings were more active than the free sulfonamides while the pyrimidine, pyridine and pyridazine complexes had similar or less activity than the free ligands. In order to find an explanation for this behavior lipophilicity and superoxide dismutase-like activity were tested, showing that the [Cu(sulfamethoxazol)2(H2O)4] . 3H2O presented the highest antimicrobial potency and a superoxide dismutase-like activity comparable with pharmacological active compounds.
Química Inorgánica, DEC, Facultad de Química, UDELAR, Gral. Flores 2124, 11800 Montevideo, Uruguay.
E
E
Kremer
G
G
Facchin
E
E
Estévez
P
P
Alborés
E J
EJ
Baran
J
J
Ellena
M H
MH
Torre
D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004926:Escherichia coli / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects; D013409:Sulfacetamide / Q000031:analogs & derivatives* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*; D013482:Superoxide Dismutase / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014867:Water / Q000737:chemistry
D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D013449:Sulfonamides; C086288:sulfacetamide copper(II) nitrate complex; D014867:Water; D013409:Sulfacetamide; D003300:Copper; D013482:Superoxide Dismutase