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Broxaterol

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Broxaterol
Names
Kekulé skeletal formula of broxaterol
IUPAC name 1-(3-Bromo-5-isoxazolyl)-2-(tert-butylamino)ethanol
Identifiers
CAS Number	76596-57-1^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2105475^Y
ChemSpider	64294^Y
ECHA InfoCard	100.071.338
MeSH	Broxaterol
PubChem CID	71149
UNII	ZE4IRB4DUC^Y
CompTox Dashboard(EPA)	DTXSID20868402
InChI InChI=1S/C9H15BrN2O2/c1-9(2,3)11-5-6(13)7-4-8(10)12-14-7/h4,6,11,13H,5H2,1-3H3^Y Key: JBRBWHCVRGURBA-UHFFFAOYSA-N^Y InChI=1/C9H15BrN2O2/c1-9(2,3)11-5-6(13)7-4-8(10)12-14-7/h4,6,11,13H,5H2,1-3H3 Key: JBRBWHCVRGURBA-UHFFFAOYAK
SMILES CC(C)(C)NCC(C1=CC(=NO1)Br)O
Properties
Chemical formula	C₉H₁₅BrN₂O₂
Molar mass	263.135 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Broxaterol is aβ₂ adrenoreceptor agonist.^[1] It is part of a class ofdrugs that affect thesmooth muscle receptors in the body, often in use cases forrespiratory disease that respond to this type of treatment.

The1,3-dipolar cycloaddition between bromonitrile oxide, producedin situ from dibromoformaldoxime, and 3-butyn-2-one gives a mixture of isoxazoles, mainly theisomer shown required for broxaterol. Selective α-bromination of the acetyl group withpyridinium tribromide gives a bromoketone whosecarbonyl group is reduced withsodium borohydride to produce a bromoethanol derivative. Treatment of this withtert-butylamine yields broxaterol.^[2]^[3]^[4]^[5]

^Nava S, Crotti P, Gurrieri G, Fracchia C, Rampulla C (January 1992)."Effect of a beta 2-agonist (broxaterol) on respiratory muscle strength and endurance in patients with COPD with irreversible airway obstruction".Chest.101 (1):133–40.doi:10.1378/chest.101.1.133.PMID 1345900. Archived fromthe original on 2013-04-14.
^US patent 4276299, Davide Della Bella and Dario Chiarino, "1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol", issued 1981-06-30, assigned to Zambon SpA
^De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Spezia, Sandro (1989). "Chemoenzymatic synthesis of chiral isoxazole derivatives".The Journal of Organic Chemistry.54 (11):2646–2650.doi:10.1021/jo00272a037.
^Rohloff, John C.; Robinson, James; Gardner, John O. (1992). "Bromonitrile oxide [3+2] cycloadditions in water".Tetrahedron Letters.33 (22):3113–3116.doi:10.1016/S0040-4039(00)79827-3.
^Battilocchio, Claudio; Bosica, Francesco; Rowe, Sam M.; et al. (2017)."Continuous Preparation and Use of Dibromoformaldoxime as a Reactive Intermediate for the Synthesis of 3-Bromoisoxazolines".Organic Process Research & Development.21 (10):1588–1594.doi:10.1021/acs.oprd.7b00229.