Pyridine analogs of 1-methyl-3-nitro-1-nitrosoguanidine and related compounds.

3-Pyridylmethyl analogs of 1-methyl-3-nitro-1-nitrosoguanidine (MNNG), 1-methyl-1-nitrosourea (MNU) and N-methyl-N-nitrosourethan (MNUT) were synthesized by nitrosation of the corresponding N-acyl-N-(3-pyridyl)methylamines. 3-Alkyl(aryl)-3-nitroso-1-(3-pyridyl)methylureas were also synthesized by nitrosation of 3-alkyl(aryl)-1-(3-pyridyl)methylureas. The reaction of some of these N-nitroso compounds with alkali, was examined. Among hese N-nitroso compounds the mutagenic activity of 3-nitro-1-nitroso-1-(3-pyridyl)methylguanidine was as potent as the ethyl analog of MNNG in the mutation assay using streptomycin-dependent E. coli Sd-4.