Complexes of salicylaldehyde acylhydrazones: cytotoxicity, QSAR and crystal structure of the sterically hindered t-butyl dimer.
A series of acylhydrazones of salicylaldehyde and their transition metal complexes, predominantly copper(II), have been prepared and characterized. The crystal structure of the Cu(II) complex of the sterically hindered t-butyl derivative contains a phenolato bridged dimer with the ligand coordinated as a tridentate moiety. QSAR analyses of the cytotoxicity of the chelators and their Cu(II) complexes reveals that solubility is the dominant factor for activity. Compounds display a maximum with respect to lipophilicity, allowing optimization of the bioactivity for both the ligands and their complexes. Copper complexes are significantly more cytotoxic than the metal-free ligands and complexes of other metals: Cu > Ni > Zn = Mn > Fe = Cr > Cr > Co.
Koh
L L
LL
Department of Chemistry, National University of Singapore.
Kon
O L
OL
Loh
K W
KW
Long
Y C
YC
Ranford
J D
JD
Tan
A L
AL
Tjan
Y Y
YY
D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D019281:Dimerization; D006801:Humans; D006835:Hydrazones / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000447:Aldehydes; D000970:Antineoplastic Agents; D006835:Hydrazones; C013243:salicylaldehyde