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Synthesis and characterization of optically pure [3H](+)azidophenazocine ([3H](+)-AZPH), a novel photoaffinity label for sigma receptors

✍ Scribed by Brian R. de Costa; Wayne D. Bowen

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
551 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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

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