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Synthesis of 3,4‐dihydro‐5‐[ 11 C]methoxy‐1(2H)‐isoquinolinone as a potential tracer for poly(ADP‐ribose) synthetase
Author(s) -
Miyake Yoshinori,
Shimadzu Hiroshi,
Hashimoto Naoto,
Ishida Yoshio,
Shibakawa Masahiko,
Nishimura Tsunehiko
Publication year - 2000
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 - 10.1002/1099-1344(200009)43:10<983::aid-jlcr383>3.0.co;2-c
Subject(s) - chemistry , sodium azide , yield (engineering) , trifluoromethanesulfonate , specific activity , stereochemistry , radiochemistry , organic chemistry , enzyme , catalysis , materials science , metallurgy
Abstract Synthesis of 3,4‐dihydro‐5‐[ 11 C]methoxy‐1(2H)‐isoquinolinone ([ 11 C]MIQO), a potent poly (ADP‐ribose) synthetase inhibitor, was devised in order to evaluate whether it is possible to image excessive activation of poly (ADP‐ribose) synthetase (PARS) by positron emission tomography. [ 11 C]MIQO was prepared by O‐[ 11 C]methylation of 3,4‐dihydro‐5‐hydroxy‐1(2H)‐isoquinolinone, obtained by a Schmidt reaction with 4‐hydroxy‐1‐indanone, sodium azide and trichloroacetic acid, with [ 11 C]methyl triflate. Total synthesis time from EOB was 35 minutes. The radiochemical yield based on [ 11 C]carbon dioxide was 31±8% (n=8; decay corrected). The final product had a specific activity of 76 GBq/μmol at EOS, and the radiochemical purity of [ 11 C]MIQO was over 99%. Copyright © 2000 John Wiley & Sons, Ltd.