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Synthesis of [ 3 H]tert‐butyl 8‐chloro‐5,6‐dihydro‐5‐methyl‐6‐oxo‐4h‐imidazo[1,5‐a][1,4]benzodiazepine 3‐carboxylate, a selective, high affinity ligand for the diazepam insensitive (DI) subtype of the benzodiazepine receptor
Author(s) -
Gu ZiQiang,
de Costa Brian R.,
Wong Garry,
Rice Kenner C.,
Skolnick Phil
Publication year - 1992
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.2580311213
Subject(s) - chemistry , carboxylate , ligand (biochemistry) , yield (engineering) , benzodiazepine , catalysis , tritium , medicinal chemistry , chemical synthesis , stereochemistry , organic chemistry , receptor , in vitro , biochemistry , materials science , physics , nuclear physics , metallurgy
The preparation of [ 3 H]‐labelled tert‐butyl 8‐chloro‐5,6‐dihydro‐5‐methyl‐6‐oxo‐4H‐imidazo[1,5‐a][1,4]benzodiazepine 3‐carboxylate (TCIB, 6 ), a high affinity ligands for the diazepam insensitive (DI) subtype of the benzodiazepine receptor (BZR) is described. Synthesis of [ 3 H]TCIB was accomplished in 4 steps starting from 5‐chloroisatoic anhydride. Tritium‐label introduction was achieved in the final step by selective catalytic tritiolysis in 62% radiochemical yield with quantitative isotopic incorporation.