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.
Highlights
Pyridine oxime O-ethers containing different heteroatomic groups are of interest as biologically active compounds
The purity of all synthesized compounds was determined by HPLC and content of impurities was not higher than 2.5%
A preliminary analysis of the structure-activity relationship for the cytotoxic action clearly indicates the strong influence of the silicon and germanium containing alkyl substituent on toxic effects in vitro
Summary
Pyridine oxime O-ethers containing different heteroatomic groups are of interest as biologically active compounds. Cytotoxicity of silicon and germanium derivatives of pyridine oxime O-ethers has not been investigated till and is the aim of the present work. Haloalkylsilane (1 mmol) was added to a suspension of pyridine oxime [1,2,3] (1 mmol), 18-crown-6 (0.026 g, 0.1 mmol) and powdered KOH (0.168 g, 3 mmol) in benzene (1 ml). Alkylation of pyridine oximes with silicon and germanium containing alkyl halides was studied.
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