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Preparation of tritium‐labeled PF‐622, a novel fatty acid amide hydrolase inhibitor
Author(s) -
Zhang Yinsheng
Publication year - 2017
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.3559
Subject(s) - chemistry , moiety , piperazine , tritium , amide , catalysis , fatty acid amide hydrolase , ring (chemistry) , isotopomers , stereochemistry , selectivity , bromide , fatty acid , organic chemistry , biochemistry , physics , receptor , cannabinoid receptor , molecule , nuclear physics , agonist
To make a detailed characterization of the mechanism of inhibition and selectivity of a novel fatty acid amide hydrolase inhibitor PF‐622 , 3 tritium isotopomers were prepared. [ 3 H] PF‐622a labeled at the piperazine ring B and [ 3 H] PF‐622b labeled at both the ring B and phenyl ring A were synthesized via catalytic H(hydrogen)‐T(tritium) exchange, utilizing 1 equiv and excess of Crabtree's catalyst, respectively. The preparation of [ 3 H] PF‐622c labeled only at the phenyl ring A was achieved via tritiodebromination of the bromide precursor, using Pd(PPh 3 ) 4 as a catalyst. The observations from these tritiation reactions might open a new perspective in the labeling for the targets having a similar moiety.