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, C13H13N3OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C14H15N3OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C18H15N3OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C14H15N3OS·C2H6OS, (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.

Wechselwirkungen in Molekülkristallen, 154 [1 - 3]. Wirt/Gast-Einschlußverbindungen von N,N'-Ditosyl-p-phenylendiamin- Derivaten: Die Kristallstrukturen von N,N'-Di(4-nitro-benzosulfuryl)-p- phenylendiamin und seinen Wasserstoffbrücken-Addukten mit Cyclopentanon, Cyclohexanon, Tetrahydrofuran, N,N-Dimethylformamidsowie Pyridin / Interactions in Molecular Crystals, 154 [1 - 3]. Host/Guest-Inclusion Compounds of N,N'-Ditosyl-p-phenylenediamine Derivatives: The Crystal Structures of N,N'-Di(4- nitro-benzosulfuryl)-p-phenylenediamine and its Hydrogen-Bonded Adducts with Cyclopentanone, Cyclohexanone, Tetrahydrofurane, N,N-Dimethylformamide as well as Pyridine

Based on preceeding investigations on the crystallization and structures of 13 inclusion compounds with a variety of guest molecules in the host matrix of N,N′-Ditosyl-p-phenylenediamine, the crystal structures of N,N′-Di(4-nitro-benzosulfuryl)-p-phenylenediamine and the five hydrogen bond acceptor molecules cyclopentanone, cyclohexanone, tetrahydrofurane, N,N-dimethylformamide, and pyridine are reported and discussed. In all of the host/guest aggregates formed, the planes of the (4-nitro)phenyl substituents are more strongly twisted out of the p-phenylene plane than in the guest-free host crystal structure, substantiating the importance of optimum conformation of the sulfonamide backbone. The dominant interactions, however, are the hydrogen bonds from the donor host to the acceptor guest, which prevent the usual formation of (sulfonamide···sulfonamide) hydrogen bond motifs in the host lattice. A pecularity is found in the 4:1 stochiometry of the pyridine inclusion compound of N,N′-di(4-nitro-benzosulfuryl)-p-phenylenediamine.