Muscimol analogues: Synthesis of isomuscimol (3-aminomethyl-5-isoxazolol) and some derivatives of azamuscimol (5-aminomethyl-3-pyrazolol) [Amanita muscaria]
1979
Hjeds, H. | Krogsgaard-Larsen, P. (Danmarks Farmaceutiske Hoejskole, Copenhagen. Dept. of Chemistry)
The syntheses of 3-aminomethyl-5-isoxazolol (isomuscimol) monohydrate (6), 5-amino-methyl-1-methyl-3-pyrazolol (1-methylazamus-cimol) dihydrochloride (18), and 5-aminomethyl-2-methyl-3-pyrazolol (2-methylazamuscimol) monohydrate (15), all of which are analogues of muscimol (5-aminomethyl-3-isoxazolol), are described. The preparations proceeded via the appropriately protected gamma-aminoacetoacetates. Isomuscimol monohydrate (6) was synthesized via Cbz- (3a) or Boc-isomuscimol (3b), acid catalyzed deprotection of which gave the beta-hydroxyimino-gamma-amino acid esters 4a and 5b, which upon treatment with triethylamine recyclized to give isomuscimol monohydrate (6). Attempts to prepare 1-acetyl-5-aminomethyl-3-pyrazobol (1-acetylazamuscimol) are also described.
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