Synthesis and characterization of optically pure [3H](+)azidophenazocine ([3H](+)‐AZPH), a novel photoaffinity label for sigma receptors
作者： Brian R. de Costa , Wayne D. Bowen
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摘要: [3H](+)-cis-N-(2-(4-Azidophenyl)ethyl) -2′-hydroxy-2,6-dimethyl-6,7-benzomorphan ([3H]1) ([3H](+)-AZPH), a novel high affinity and selectivity benzomorphan based photoaffinity label for sigma receptors was synthesized in 4 steps starting with optically pure (+)-normetazocine 2-(p-azidophenyl)ethyl methanesulfonate ester. Condensation of these compounds DMF the presence NaHCO3 afforded 1 77% yield. The tritiation precursor (+)-cis-N-(2-(4-azidophenyl)ethyl)-2′-hydroxy-1′,3′-dibromo-2,6-dimethyl-6,7- (4) medium specific activity [3H]1 obtained 96% yield by bromination 2 equivalents bromine. sequence catalytic 4, treatment resulting aniline ([3H]5) (13.5% radiochemical yield, 22.9 Ci/mmol) nitrous acid followed sodium azide target compound 78% chemical
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