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Synthesis and anti-tetrabenazine activity of c-3 analogues of dimethyl-2-phenylmorpholines
- Source :
- Journal of Heterocyclic Chemistry. 33:33-39
- Publication Year :
- 1996
- Publisher :
- Wiley, 1996.
-
Abstract
- A series of analogues of 2-phenylmorpholines with alkyl substituents at the C-3 position were synthesized for anti-tetrabenazine (anti-TBZ) testing in mice. The target compounds were prepared by reaction of (2-bromoalkyl) phenyl ketones 21a-h with the appropriate aminoalcohol 20a-b to form morpholinols 22a-h. Hydride reduction of the morpholinols gave aminodiols 23a-h which were cyclized to morpholines 6, 8, 10–12, 14–16, 18 and 19 by acid catalaysis. Compounds 7, 9, 13 and 17 were prepared by reductive formylation. The smaller straight chain substituents of 6, 8, 12 and 15, and the beta branching of the iso-butyl group of 16 were well tolerated; anti-tetrabenazine ED50′s were comparable to compounds 2–5. The α-branched, N-methylated, and side chain aryl derivatives were less active.
Details
- ISSN :
- 19435193 and 0022152X
- Volume :
- 33
- Database :
- OpenAIRE
- Journal :
- Journal of Heterocyclic Chemistry
- Accession number :
- edsair.doi...........7022b12ac437e54955935638cb567577
- Full Text :
- https://doi.org/10.1002/jhet.5570330106