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Synthesis, in vitro pharmacology and radiosynthesis of N ‐( cis ‐4‐fluoromethylcycloyhexyl)‐4‐(1(H)‐imidazol‐4‐yl)piperidine‐11‐thiocarbonamide (VUF 5000), a potential PET ligand for the histamine H 3 receptor
Author(s) -
Windhorst Albert D.,
Timmerman Henk,
Menge Wiro M. P. B.,
Leurs Rob,
Herscheid Jacobus D. M.
Publication year - 1999
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/(sici)1099-1344(199903)42:3<293::aid-jlcr191>3.0.co;2-b
Subject(s) - chemistry , piperidine , radiosynthesis , thioperamide , histamine , stereochemistry , ligand (biochemistry) , in vivo , in vitro , chemical synthesis , histamine h3 receptor , antagonist , receptor , pharmacology , biochemistry , medicine , microbiology and biotechnology , biology
The synthesis of N ‐( cis ‐4‐fluoromethylcyclohexyl)‐4‐(1(H)‐imidazol‐4‐yl)piperidine‐1‐thiocarbonamide (VUF 5000) 3 , a fluorinated analogue of the potent (pA 2 value of 8·9±0·1, K i =4·3±0·9 nM) histamine H 3 receptor antagonist thioperamide 2 is described. After the establishment of the H 3 antagonistic activity of VUF 5000, pA 2 value=9·0±0·2, K i =2·3±0·5 nM, a four step synthesis for the radiolabelling of VUF 5000 with 18 F (half life 110 min) was developed. Within 4 hours of the end of the bombartment, [ 18 F]VUF 5000 was obtained with an average radiochemical yield of 23% (decay corrected) and a specific activity >96·2 TBq/μmol (2·6 Ci/μmol). Copyright © 1999 John Wiley & Sons, Ltd.