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A general synthetic method suitable for the introduction of deuterium or tritium in buspirone type anxiolytic agents
Author(s) -
Welch Willard M.,
Viverios D. M.
Publication year - 1989
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580270613
Subject(s) - buspirone , chemistry , anxiolytic , tritium , combinatorial chemistry , reagent , chemical synthesis , stereochemistry , organic chemistry , in vitro , biochemistry , receptor , physics , nuclear physics , agonist
Abstract In recent years, a number of putative non‐benzodiazepine anxiolytic agents incorporating the 4‐ aminobutylimide or sulfonamide‐imide linkage have been reported and at least two of these, buspirone and gepirone, have been shown to have anxiolytic activity in man. In order to study the metabolism, body distribution and binding affinities of this class of compound, it was of interest to devise a precursor which could be specifically labelled with tritium to high specific activity. We have devised a synthetic route to the corresponding but‐2‐ynyl and but‐2‐enyl analogs of gepirone and have converted the latter to dideuterogepirone as an example of the methodology. Thus the method chosen has been found to be practical and is believed to be of sufficient generality to enable the synthesis of a variety of derivatives of this type containing either two or four atoms of label. Furthermore by appropriate choice of reagents, incorporation of 14 C into these compounds may be achieved.