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14C-labeling of a tetrahydroacridine, a novel CNS-selective cholinesterase inhibitor

✍ Scribed by Kazuhiko Nishioka; Takeshi Kamada; Hiroshi Kanamaru

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
298 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

9‐Amino‐8‐fluoro‐2, 4‐methano‐1,2,3,4‐tetrahydroacridine citrate (SM‐10888), a novel cholinesterase inhibitor, was labeled with carbon‐14 at C9 of the tetrahydroacridine ring for use in metabolic studies. Carbonation of 2,6‐difluorophenyllithium (3) with [^14^C]carbon dioxide gave the acid (4). Chlorination of 4 followed by treatment of the resulting acid chloride with ammonia afforded the amide (5). Dehydration of 5 with thionyl chloride and subsequent displacement reaction with ammonia gave the aminobenzonitrile (7). Condensation of 7 with the ketone (8) in the presence of anhydrous zinc chloride yielded the aminoacridine (9), which was treated with citric acid to afford [9‐^14^C]SM‐10888 (1). The overall yield of 1 was 37% from 2, and the specific activity was 1.35 GBq/mmol.

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