Collect. Czech. Chem. Commun. 1985, 50, 470-481

Reactions of 1-(5-nitro-2-furyl)-2-nitroethylene with amino and hydroxy groups

Michal Rosenberga, Ernest Šturdíka, Tibor Liptajb, Juraj Bellab, Daniel Véghc, František Považanecc and Vladimír Sitkeya

a Department of Technical Microbiology and Biochemistry
b Department of Physical Chemistry
c Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Institute of Technology, 812 37 Bratislava


Reactions have been studied of l-(5-nitro-2-furyl)-2-nitroethylene with -NH, and -OH groups of low-molecular compounds (butylamine, aniline, glycine, taurine, glucosamine, tyramine, tryptamine, noradrenaline, histamine, ethanol, methanol, OH- ions) as well as biopolymers (ribonuclease, albumin DNA, RNA, Newcastle disease virus). With the low-molecular amines and alcohols it has been found that the reactions proceed as nucleophilic additions in aqueous medium, and the respective nucleophilic groups attack the more electrophilic C(1) atom of the exocyclic double bond of nitrofurylethylene. The modifications proved with the above-mentioned biopolymers in vitro indicate a possibility of direct interaction (without metabolic activation) between 5-nitro-2-furylethylenes and proteins or nucleic acids in vivo. These findings are significant from the point of view of recognizing mutagenic effect of nitrofurylethylenes and general biotoxicity of these compounds.