Talk:Substituted 3-hydroxyisoxazoles: Difference between revisions
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==Chemistry== | ==Chemistry== | ||
3-Hydroxyisoxazoles are a class of organic compounds that feature an isoxazole ring substituted with a hydroxyl group at the 3-position. The isoxazole ring itself is a five-membered heterocycle containing an oxygen atom and a nitrogen atom in adjacent positions. 3-Hydroxyisoxazoles can exhibit tautomerism, where the hydroxyl group can tautomerize to a keto form, resulting in a 3-isoxazolone structure. | 3-Hydroxyisoxazoles are a class of organic compounds that feature an isoxazole ring substituted with a hydroxyl group at the 3-position. The isoxazole ring itself is a five-membered heterocycle containing an oxygen atom and a nitrogen atom in adjacent positions. 3-Hydroxyisoxazoles can exhibit tautomerism, where the hydroxyl group can tautomerize to a keto form, resulting in a 3-isoxazolone structure<ref>{{Citation | title=New approach to 3-hydroxyisoxazole-5-carbaldehydes: key intermediates in the synthesis of new 3-hydroxyisoxazoles of pharmacological interest | url=https://www.ch.ic.ac.uk/ectoc/echet96/papers/059/index.htm}}</ref>. | ||
==Pharmacology== | ==Pharmacology== | ||
[[File:Muscimol vs GABA 3D.png|231px|thumb|right|GABA and muscimol molecules can have similar 3D-conformations which are shown superimposed in this image.]] | |||
Most of the known 3-hydroxyisoxazoles may be regarded as conformationally restricted bio-isosteres of [[neurotransmitters]] such as [[gamma-aminobutyric acid]] (GABA), [[glutamic acid]] or [[N-methyl-D-aspartic acid]] (NMDA). Muscimol, gaboxadol and GABA are in their bioactive conformations, because of this similarity, muscimol and gaboxadol bind to certain GABA-receptors. | |||
==List of substituted 3-hydroxyisoxazoles== | ==List of substituted 3-hydroxyisoxazoles== | ||
Revision as of 00:03, 16 February 2025
Substituted 3-hydroxyisoxazoles (also known as 3-hydroxyisoxazoles, 3-isoxazolols or 3-isoxazolones) is a chemical class of organic compounds based on the 3-hydroxyisoxazole structure. Members of this class typically act on GABA and glutamate receptors. The best known members of this class are muscimol and ibotenic acid, alkaloids from Amanita muscaria, gaboxadol, a synthetic derivative of muscimol, and AMPA, a synthetic AMPA receptor agonist[1].
Chemistry
3-Hydroxyisoxazoles are a class of organic compounds that feature an isoxazole ring substituted with a hydroxyl group at the 3-position. The isoxazole ring itself is a five-membered heterocycle containing an oxygen atom and a nitrogen atom in adjacent positions. 3-Hydroxyisoxazoles can exhibit tautomerism, where the hydroxyl group can tautomerize to a keto form, resulting in a 3-isoxazolone structure[2].
Pharmacology
Most of the known 3-hydroxyisoxazoles may be regarded as conformationally restricted bio-isosteres of neurotransmitters such as gamma-aminobutyric acid (GABA), glutamic acid or N-methyl-D-aspartic acid (NMDA). Muscimol, gaboxadol and GABA are in their bioactive conformations, because of this similarity, muscimol and gaboxadol bind to certain GABA-receptors.
List of substituted 3-hydroxyisoxazoles
| Compound | R4 | R5 | Structure |
|---|---|---|---|
| Muscimol | H | CH2NH2 | 
|
| Ibotenic acid | H | CH(NH2)C(O)OH | 
|
| Gaboxadol | CH2CH2- | CH2NH- | 
|