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Novel 2,4,5‐Trisubstituted Pyridines as Key Intermediates for the Preparation of the TSPO Ligand 6‐F‐PBR28: Synthesis and Full 1 H and 13 C NMR Characterization
Author(s) -
Damont Annelaure,
Lemée Frédéric,
Raggiri Guillaume,
Dollé Frédéric
Publication year - 2014
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.1723
Subject(s) - chemistry , translocator protein , ligand (biochemistry) , stereochemistry , combinatorial chemistry , receptor , medicine , biochemistry , neuroinflammation , inflammation
As part of our ongoing research for molecular structures binding to the translocator protein (TSPO 18 kDa), we investigated the preparation of a number of new 2,4,5‐trisubstituted pyridines as novel building blocks . In particular, 5‐amino‐2‐halo‐4‐phenoxypyridines ( 11 , 12 , 13 ) were designed as key intermediates for the synthesis of the recently developed TSPO ligand 6‐F‐PBR28 and its fluorine‐18‐labeled version for positron emission tomography, 6‐[ 18 F]F‐PBR28. We hereby report the chemical preparation as well as the 1 H and 13 C NMR spectroscopic data of polysubstituted pyridines 2 , 3 , 4 , 5 , 6 , 7 , 7b , 8 , 9 , 10 , 11 , 12 , 13 , 14 . The latter demonstrates dramatic changes in electron density repartition of the aromatic ring upon substitution.