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PubMed1991

[Synthesis and central effects of 4-hydroxy-(alkyl)- and 4-amino-(alkyl)-substituted 2,6-epoxy-3-benzoxocines].

The tricyclic hemiacetal 1 is transformed with amines to the N/O-acetals 3 and 10, with nitromethane to the 4-nitromethyl derivative 13, and with the Wittig reagents 15a and 15b to the 2-benzopyrans 16 and 19. Reduction and methylation of 13 yield the tertiary amine 4; through three steps the secondary amine 18 and the tertiary amine 5 are prepared from 16 and 19, respectively. The 1,3-dioxane ring of all these 2,6-epoxy-3-benzoxocine derivatives exists in the chair conformation with an equatorial C-4 substituent. After application of the amines 5, 11c, and 18 mice do not show any symptoms of central activity; weak CNS-effects are observed with the alcohols 1 and 2. For the tertiary amine 4, which causes considerable central effects (Straubtail-phenomenon, convulsions, etc.), an ED50 of 78 mg/kg is determined in the mouse "writhing"-test.

Analgesics↗