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Synthesis of high specific activity tritium labeled ( E )‐6‐(bromomethylene)‐tetrahydro‐3‐(1‐naphthalenyl)‐2 H ‐pyran‐2‐one as a selective probe for calcium‐independent phospholipase a 2
Author(s) -
Durley Richard C.,
Parnas Barry L.,
Weiss Randy H.
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.2580310907
Subject(s) - chemistry , pyran , tritium , yield (engineering) , bicyclic molecule , acetic acid , specific activity , naphthalene , stereochemistry , calcium , organic chemistry , enzyme , physics , materials science , nuclear physics , metallurgy
The synthesis of ( E )‐6‐(bromomethylene)‐tetrahydro‐3‐([4‐ 3 H]‐1‐naphthalenyl)‐2 H ‐pyran‐2‐one at a specific activity of 24.0 Ci/mmol is described. This probe was synthesized to determine whether ( E )‐6‐(bromomethylene)‐tetrahydro‐3‐(1‐naphthalenyl)‐2 H ‐pyran‐2‐one inhibits calcium‐independent myocardial phospholipase A 2 irreversibly via covalent modification. The material was synthesized in four steps from 1‐naphthalene acetic acid via [4‐ 3 H]‐1‐naphthaleneacetic acid. The yield from [4‐ 3 H]‐1‐naphthaleneacetic acid was 29.7%. The radiochemical purity of the HPLC‐purified final product was 99.5%.