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Isoxazole

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Isoxazole
Full structural formula
Skeletal formula with numbers
Ball-and-stick model
Space-filling model
Names
IUPAC name
1,2-oxazole
Other names
isoxazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.472 Edit this at Wikidata
UNII
  • InChI=1S/C3H3NO/c1-2-4-5-3-1/h1-3H checkY
    Key: CTAPFRYPJLPFDF-UHFFFAOYSA-N checkY
  • InChI=1/C3H3NO/c1-2-4-5-3-1/h1-3H
    Key: CTAPFRYPJLPFDF-UHFFFAOYAS
  • n1occc1
Properties
C3H3NO
Molar mass 69.06202 g/mol
Density 1.075 g/ml
Boiling point 95 °C (203 °F; 368 K)
Acidity (pKa) -3.0 (of conjugate acid) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Isoxazole is an azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the univalent radical derived from isoxazole.

Occurrence

Isoxazole rings are found in some natural products, such as ibotenic acid and muscimol.

Pharmaceuticals and herbicides

Isoxazoles also form the basis for a number of drugs,[2] including the COX-2 inhibitor valdecoxib (Bextra) and a neurotransmitter agonist AMPA. A derivative, furoxan, is a nitric oxide donor. An isoxazolyl group is found in many beta-lactamase-resistant antibiotics, such as cloxacillin, dicloxacillin and flucloxacillin. Leflunomide is an isoxazole-derivative drug. Examples of AAS containing the isoxazole ring include danazol and androisoxazole. A number of pesticides are isoxazoles.[3]

Isoxaben is an example of an isoxazole used as a herbicide.

See also

References

  1. ^ Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).
  2. ^ "The recent progress of isoxazole in medicinal chemistry". Bioorganic & Medicinal Chemistry. 26 (12): 3065–3075. 2018. doi:10.1016/j.bmc.2018.05.013. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  3. ^ Clemens Lamberth (2018). "Oxazole and Isoxazole Chemistry in Crop Protection". Journal of Heterocyclic Chemistry. 55 (9): 2035–2045. doi:10.1002/jhet.3252. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
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