Synthesis and biological activity of (hydroxymethyl)- and (diethylaminomethyl)benzopsoralens.
J Med Chem
; 42(15): 2936-45, 1999 Jul 29.
Article
em En
| MEDLINE
| ID: mdl-10425103
ABSTRACT
Some benzopsoralens, carrying a hydroxymethyl or a diethylaminomethyl group at the 3, 5, 8, and 11 positions, were prepared, and their biological activity was compared with that of 4-(hydroxymethyl)benzopsoralen (BP). 5-(Hydroxymethyl)benzopsoralen (7b), 11-(hydroxymethyl)benzopsoralen (7c), and 11-(diethylaminomethyl)benzopsoralen (8c) induced marked antiproliferative effects in mammalian cells by simple incubation in the dark; this activity appeared to be related to their ability to inhibit topoisomerase II. Benzopsoralens appeared to be more active, especially BP and 7c, upon UVA activation. Compounds carrying a methyl group at the 4 position together with a hydroxymethyl or diethylaminomethyl at the 8 position (7d and 8d, respectively) were also effective, although to a lower extent; instead, a substituent at the 3 position canceled all activity. Benzopsoralens did not induce interstrand cross-links in DNA in vitro, as seen in the induction of cytoplasmic <
Buscar no Google
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Furocumarinas
/
Fármacos Fotossensibilizantes
/
Inibidores Enzimáticos
Idioma:
En
Ano de publicação:
1999
Tipo de documento:
Article