engleski

Sodium and potassium benzeneazophosphonate complexes with crown ethers: solid-state microwave synthesis, characterization and biological activity

The eco-friendly synthesis, spectroscopic (IR, MS, 1H and 13C NMR) study and biological (cytostatic, antiviral) activity of sodium and potassium benzeneazophosphonate complexes obtained by reaction in the solid state under microwave irradiation of alkali salts of ethyl [4-alpha-(benzeneazoanilino)-N-benzyl]phosphonic acid and [alpha-(benzeneazoanilino)-N-4-methoxybenzyl]phosphonic acid with crown ethers containing the 18-membered (dibenzo-18-crown-6 and bis(4'-di-tert-butylbenzo)-18-crown-6), 24-membered (dibenzo-24-crown-8) and 30-membered (dibenzo-30-crown-10) macrocyclic ring, have been described. The simple work-up solvent free reaction is an efficient green procedure for formation of the mononuclear crown ether complexes in which the sodium/potassium ion is bound to oxygen atoms of the macrocycle and the phosphonic acid oxygen. The free crown ethers, alkali benzeneazophosphonate salts and their complexes were evaluated for their cytostatic activity in vitro against the murine leukemia L1210, the murine mammary carcinoma FM3A and the human T-lymphocyte CEM and MT-4 cell lines, as well as for their antiviral activity against a wide variety of DNA and RNA viruses. The investigated compounds showed no specific antiviral activity, whereas all free crown ethers and their complexes demonstrated cytostatic activity, which was especially pronounced in the case of bis(4'-di-tert-butylbenzo)-18-crown-6 and its complexes.

crown ether ; sodium ; potassium ; benzeneazophosphonate complex ; cytostatic activity ; antiviral activity

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