Synthesis and Cytotoxicity of Silicon and Germanium Containing Pyridine Oxime O-Ethers

Abstract

Silicon and germanium containing pyridine aldoxime, ketoxime and amidoxime O-ethers have been prepared using phase transfer catalytic systems oxime alkyl halide solid KOH 18-crown-6 benzene and oxime alkyl halide solid K₂CO₃ or Cs₂CO₃ 18-crown-6 toluene. Cytotoxic activity of silicon and germanium containing pyridine oxime O-ethers was tested in vitro on two monolayer tumor cell lines: MG- 22A (mouse hepatoma) and HT-1080 (human fibrosarcoma). O-[3-Yriethylsilylpropyl]- and O-[3-(1-methyl- 1-silacyclopentyl)propyl] oximes of pyridine aldehydes and ketones exhibit high cytotoxicity. Presence of methyl group in the pyridine ring considerably decreased activity of amidoxime O-ethers. Oxime ethers containing two elements are essentially inactive. For 2-acetylpyridine oxime ethers the activity increases in order of alkyl substituents: Et₃GeCH₂CH₂SiMe₂CH₂ < Et₃SiCH₂CH₂CH₂ < (CH₂)₄SiCH₂CH₂CH₂. Cytotoxicity of ketoxime O-ethers is considerably lower in comparison with aldoxime O-ethers.

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