Influence of methoxy and nitro groups in the oxidative metabolism of naphtho[2,1-b]furan.
In the present study, we have investigated the role of methoxy and nitro groups in the oxidative metabolism of naphtho[2,1-b]furan. Hepatic microsomes were used to investigate the aerobic metabolism of naphtho[2,1-b]furan (compound A), 2-nitro-naphtho[2,1-b]furan (compound B) and 7-methoxy-naphtho [2,1-b]furan (compound C) and comparison of the metabolites formed was made using HPCL analysis and NMR, mass and UV-visible spectrometry. The different metabolic pathways investigated were compared with the previously reported metabolism of 7-methoxy-2-nitro-naphtho[2,1-b]furan (compound D). Naphtho[2,1-b]furan yield metabolites of both the furan and benzene rings, while metabolites formed from 7-methoxy-naphtho[2,1-b]furan and 2-nitro-naphtho [2,1-b]furan were derived entirely as a result of enzymic attack on the first benzene ring.
Strapelias
H
H
Laboratoire de Physique et Chimie Biomoléculaire URA CNRS 198, Institut Curie (Section de Physique et Chimie), Paris, France.
Tabet
J C
JC
Prigent
Y
Y
Lecoq
S
S
Duquesne
M
M
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D005663:Furans / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D009153:Mutagens / Q000378:metabolism*; D009281:Naphthalenes; D009581:Nitrofurans / Q000378:metabolism; D010084:Oxidation-Reduction; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D005663:Furans; D009153:Mutagens; D009281:Naphthalenes; D009581:Nitrofurans; C075195:naphtho(2,1-b)furan; C053501:2-nitronaphtho(2,1-b)furan; C053502:7-methoxynaphtho(2,1-b)furan