Assessment of mutagenic potential in a series of compounds structurally related to 2-amino-3-methylimidazoquinoline (IQ)

Article abstract of DOI:10.1016/0223-5234(93)90085-S

The bacterial mutagenicity of a series of compounds related to the mutagen 2-amino-3-methylimidazo<4,5-f>quinoline (IQ) was determined in the Ames test using Salmonella strain TA-1538.Thiazolo<4,5-f>quinoline-2-amine 3 and its 4,5-dihydro derivative 4, where the N(3)-Me moiety of IQ has been replaced by a sulfur atom, were both potent mutagens.A structure-mutagenicity study was performed in a group of aminothiazole compounds related to 3.In addition to the aromatic NH2 group, a fully aromatic tricyclic structure is required for mutagenicity.Enzymatic oxidation canprovide the required aromaticity to partially reduced analogues, but more extensively reduced compounds, or compounds where the central ring cannot be oxidized, are not mutagenic. - Keywords: mutagenicity / Ames / IQ / aminothiazole