Synthesis and cytotoxic activity of 1-{3-[1-(5-organylsilylfuran-2-yl)silinan-1-yl]propyl}amines and some trimethylgermyl analogues

Chemistry. 2014 Sep 26;20(40):12786-8. doi: 10.1002/chem.201402865. Epub 2014 Aug 8.

Abstract

New highly cytotoxic 1-{3-[1-(5-organylsilyl-furan-2-yl)silinan-1-yl]propyl}amines and some trimethylgermyl analogues (IC50 1-7 μg mL(-1)) have been synthesized by a hydrosilylation reaction of aliphatic and heterocyclic N-allylamines in the presence of Speier's catalyst. The effects of the silacycle, the element-organic substituent in position 5 of the furan ring, and the structure of the amine on the cytotoxicity of the new compounds have been studied.

Keywords: 29Si NMR spectroscopy; cytotoxicity; furylsilinanes; silicon chemistry; toxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Germanium / chemistry*
  • Germanium / pharmacology*
  • Humans
  • Methylation
  • Mice
  • NIH 3T3 Cells
  • Neoplasms / drug therapy
  • Organosilicon Compounds / chemical synthesis
  • Organosilicon Compounds / chemistry*
  • Organosilicon Compounds / pharmacology*

Substances

  • Antineoplastic Agents
  • Organosilicon Compounds
  • Germanium