Novel trialkylsilyl(germyl)-substituted thienyl- and furylbenzimidazoles and their N-substituted derivatives – synthesis, structure and cytotoxic activity

Authors:
  • LILuba Ignatovich
    Luba Ignatovich
  • OSOlga Starkova
    Olga Starkova
  • VRVitalijs Romanovs
    Vitalijs Romanovs
  • ISIlze Sleiksha
    Ilze Sleiksha
  • ISIrina Shestakova
    Irina Shestakova
  • JPJury Popelis
    Jury Popelis
  • ELEdmunds Lukevics
    Edmunds Lukevics
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Abstract
The reaction of 1,2-phenylenediamine with a variety of silicon- or germanium-containing 2-furaldehydes or 2-thienylcarbaldehydes in DMFA gave the corresponding benzimidazole derivatives in moderate yields (36–49%) in the presence of sodium hydrogen sulfite. As a result, a new series of silyl, germyl substituted hetarylbenzimidazoles were synthesized and their in vitro cytotoxicity was studied. The quaternisation of N-substituted benzimidazoles by heating with various alkyl, allyl and propargyl chlorides and bromides leads to the formation of benzimidazolinium salts. Potential cytotoxic activity of synthesized new benzimidazoles and benzimidazolinium salts was tested in vitro on two monolayer tumour cell lines: MG-22A (mouse hepatoma), HT-1080 (human fibrosarcoma) and normal mouse fibroblasts (NIH 3T3) and compared with corresponding benzimidazoles.

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