[Biotransformation of aza-3-chalcol in the rat: isolation and structural analysis of seven metabolites].
The azachalcol 3-phenyl-1-(3-pyridinyl)prop-2-en-1-ol S-1 has been used to investigate the metabolic profile in rat. Seven metabolites and the unchanged substance were isolated from urine. The biotransformation products were extracted and purified by chromatography (LC, CTLC, HPLC) and identified by comparison with some synthetic reference compounds or by spectroscopic analysis (UV, IR, 1H, 13C NMR and MS). A scheme of potential metabolic pathway is proposed. It appears that three specific targets of the parent molecule are extensively oxidized. Thus the aromatic heterocycle yields three N-oxides (M-4, M-5, M-7). The deshydrogenation of the secondary alcoholic group to the ketone is also observed (M-2). Finally, the ethylenic double bond is a favored site for hydroxylation (M-7, M-8) as well as reduction (M-3, M-4, M-6).
Morand
J M
JM
Laboratoire de Chimie Thérapeutique, UFR de Pharmacie-UJF Grenoble I, La Tronche.
Cussac
M
M
Kaouadji
M
M
Thomasson
F
F
D000818:Animals; D001711:Biotransformation; D008297:Male; D011725:Pyridines / Q000737:chemistry* / Q000493:pharmacokinetics; D051381:Rats; D017208:Rats, Wistar
D011725:Pyridines; C029864:1-(3-pyridyl)-1-hydroxy-3-phenyl-2-propene
Biotransformation de l'aza-3 chalcol chez le rat: isolement et analyse structurale de sept métabolites.