Effect of omega-trifluorination on the microsomal metabolism of ethyl and pent-1-yl p-nitrophenyl ether.
p-Nitrophenyl pent-1-yl ether was metabolized (65-70%) in the presence of liver microsomes from phenobarbital-treated rats to give the 4-(major), 3-(minor), and 2-hydroxypent-1-yl (minor) derivatives which were characterized by g.l.c.-mass spectrometry; O-dealkylation (reflecting 1-hydroxylation) and 5-hydroxylation did not occur to a significant extent. 5,5,5-Trifluorination of the pent-1-yl group markedly reduced the extent of metabolism (to approximately 10%). p-Nitrophenyl 2,2,2-trifluoroethyl ether was virtually completely resistant to microsomal metabolism under conditions where the ethyl analogue was extensively O-dealkylated.
M H
MH
Baker
A B
AB
Foster
F
F
Leclercq
M
M
Jarman
M G
MG
Rowlands
J C
JC
Turner
D000818:Animals; D001711:Biotransformation; D005461:Fluorine; D008401:Gas Chromatography-Mass Spectrometry; D006900:Hydroxylation; D066298:In Vitro Techniques; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D009578:Nitrobenzenes / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D009578:Nitrobenzenes; D005461:Fluorine; C048578:4-nitrophenyl pent-1-yl ether; C013154:4-nitrophenetol