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Sythesis of deuterium and tritium labeled psoralens

✍ Scribed by Stephen T. Isaacs; Henry Rapoport; John E. Hearst

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
459 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Deuterium and tritium labeled 4,5′,8‐trimethylpsoralen (), psoralen (), and angelicin (), have been prepared by D~2~O and T~2~O exchange with specific activities of 228‐253 mCi/mmol. Tritium labeled 4,5′,8‐trimethylpsoralen () with a specific activity of 17.6 Ci/mmol was prepared by catalytic reduction with tritium gas followed by dehydrogenation. Tritiated 4′‐hydroxymethyl‐4,5′,8‐trimethylpsoralen () with a specific activity of 12.0 Ci/mmol was obtained by reduction of the corresponding aldehyde with sodium borotritide and elaborated to 4′‐aminomethyl‐4,5′,8‐trimethylpsoralen () (12.0 Ci/mmol) by conversion of to the chloromethyl derivative followed by the Gabriel synthesis. Tritium labeled 8‐methoxypsoralen () was prepared by demethylation of unlabeled to the phenol followed by methylation with tritiated methyl iodide.

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