Structure-mutagenicity relationships of 5-nitro-2-furylethylenes in Salmonella typhimurium TA98.

Mutagenicity of three selected series of 2-furylethylene was determined by the Ames test. These included: nine alkylesters and eleven N-alkylamides of 5-nitro-2-furylacrylic acid (NFAA) and ten derivatives differing not only at exocyclic double bond, but also in the position 5 of the furan ring. Mutagenicity of the derivatives depends on the presence of the 5-nitro-furan centre in the molecule; side chains in the position 2 modify the degree of mutagenicity. Among the derivatives of NFAA tested as changing the substituents virtually does not affect chemical properties of the 5-nitrofuran ring. Mutagenicity of the n-alkyl congeners decreases linearly with increasing lipophilicity. Mutagenicity of the derivatives with branched alkyl substituents is lower than expected from the behaviour of the n-alkyl homologues.