Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

Paul V. Bernhardt, Lorraine M Caldwell, David B Lovejoy, Des R. Richardson

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)629-633
Number of pages5
JournalActa Crystallographica. Section C: Crystal Structure Communications
Issue numberPt 11
Publication statusPublished - Nov 2003
Externally publishedYes


  • Antineoplastic Agents
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Iron Chelating Agents
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes
  • Thiosemicarbazones
  • Journal Article
  • Research Support, Non-U.S. Gov't


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