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Nuclear hydroxylated metabolite of fluradoline (2‐fluoro‐11‐[(β‐methylamino)ethylthio]dibenz[ b,f ]oxepin hydrochloride). Identification and synthesis
Author(s) -
Agnew Marc N.,
Rizwaniuk Anastasia,
Ong Helen H.,
Wichmann J. K.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230155
Subject(s) - chemistry , metabolite , hydroxylation , hydrochloride , stereochemistry , derivative (finance) , organic chemistry , biochemistry , enzyme , financial economics , economics
Fluradoline (2‐fluoro‐11‐[β‐(methylamino)ethylthio]dibenz[ b,f ]oxepin), a novel analgesic with an unique profile, was found to be extensively metabolized in man as well as in other species. One of the major metabolites of this drug appeared to be a nuclear hydroxylated derivative of the parent compound, and the site of enzymatic hydroxylation was established to be C(7) by using high‐field proton nuclear magnetic spectroscopy. This structural assignment was subsequently confirmed by the synthesis of an authentic sample of 2‐fluoro‐7‐hydroxy‐11‐[β‐(methylamino)ethylthio]dibenz[ b,f ]oxepin ( 2a ).