Structure-activity relationships in mutagenicity and in nucleophilic ring opening of N-(arylmethyl)phenanthrene 9,10-imines.
Mutagenesis
; 5(1): 25-30, 1990 Jan.
Article
en En
| MEDLINE
| ID: mdl-2184306
Ten derivatives of N-benzylphenanthrene 9,10-imine with different substituents on the phenyl ring were synthesized and subjected to mutagenicity tests in Salmonella typhimurium TA100. While electron donating groups were found to enhance the biological activity, electron attracting and bulky substituents lowered the mutagenic potency. A similar dependence on the electronic structure was observed in triethylamine/acetonitrile-promoted interaction of the title imines and 4-nitrothiophenol. This similarity suggests that both biochemical and chemical processes involve mechanisms in which protonation of the aziridine nitrogen is rate controlling, and the attack of the cellular or model nucleophile is a fast step. In contrast to these processes, the reaction of the imines with 4-nitrothiophenol in the presence of 1,5-diazabicyclo[4.3.0] non-5-ene proved to proceed by an SN2 mechanism and to be enhanced by electron attracting substituents.
Buscar en Google
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Fenantrenos
/
Iminas
/
Mutación
Idioma:
En
Revista:
Mutagenesis
Asunto de la revista:
GENETICA MEDICA
/
SAUDE AMBIENTAL
Año:
1990
Tipo del documento:
Article
País de afiliación:
Israel
Pais de publicación:
Reino Unido