Assessment of mutagenic potential in a series of compounds structurally related to 2-amino-3-methylimidazo [4,5-f]quinoline (IQ)

Autor: Lawrence D. Wise, Bradley William Caprathe, J.C. Theiss, M.L. Kropko, Juan C. Jaen, S. Wold
Rok vydání: 1993
Předmět:
Zdroj: European Journal of Medicinal Chemistry. 28:547-553
ISSN: 0223-5234
DOI: 10.1016/0223-5234(93)90085-s
Popis: 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 Thiazolo[4,5- f ]quinoline-2-amine 3 and its 4,5-dihydro derivative 4 , where the N (3)-Me moiety of IQ has been replaced by a sulfur atom, were both potent mutagens.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 NH 2 group, a fully aromatic tricyclic structure is required for mutagenicity. Enzymatic oxidation can provide the required aromaticity to partially reduced analogues, but more extensively reduced compounds, or compounds where the central ring cannot be oxidized, are not mutagenic.
Databáze: OpenAIRE