Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde.
The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C(13)H(13)N(3)OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C(14)H(15)N(3)OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C(18)H(15)N(3)OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C(14)H(15)N(3)OS.C(2)H(6)OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.
Bernhardt
Paul V
PV
Department of Chemistry, The University of Queensland, Brisbane, Queensland 4072, Australia. p.bernhardt@uq.edu.au
Caldwell
Lorraine M
LM
Lovejoy
David B
DB
Richardson
Des R
DR
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007502:Iron Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*
C495462:2-hydroxynaphthalene-1-carboxaldehyde; D000970:Antineoplastic Agents; D007502:Iron Chelating Agents; D009281:Naphthalenes; D013882:Thiosemicarbazones