Synthesis And Biological Evaluation Of Diamines Containing Monosaccharides

Author(s): Afaf R.Genady

A convenient synthetic route to diglycosylamines derived from aliphatic diamines [NH2(CH2)nNH2, where n=2,3, and 4] and α-D-glucose or Dribose is presented . In a one step process, treatment of diamines with α- D-glucose and D-ribose in methanol in the presence of a catalytic amount of glacial acetic acid gave N,N′-diglycosylamines in high yield. The structures of the new compounds were confirmed by elemental analysis, IR, NMR, and mass spectrometry. The in vitro toxicity studies using B16 melanoma cells showed that N, ′-Di-α-D-ribofuransoyl 1,2-ethanediamine, N,N′-Di-α-D-ribofuransoyl 1,3-propanediamine as well as N,N′-Di-α- D-ribofuransoyl 1,4-butanediamine are not toxic at low concentration (LD50 > 6 mM). The toxicity values for N,N′-Di-α-D-glucopyansoyl 1,2- ethanediamine, N,N′-Di-α-D-glucopyansoyl 1,3-propanediamine, and N,N′-Di-α-D-glucopyansoyl 1,4-butanediamine were lower than that of compounds rest compounds. It was observed that the toxicity increases with increasing number of carbon atoms in the chain of diamines.

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