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Epanolol

From Wikipedia, the free encyclopedia
Epanolol
Names
IUPAC name
(RS)-N-[2-([3-(2-cyanophenoxy)-2-hydroxypropyl]amino)ethyl]-2-(4-hydroxyphenyl)acetamide
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C20H23N3O4/c21-12-16-3-1-2-4-19(16)27-14-18(25)13-22-9-10-23-20(26)11-15-5-7-17(24)8-6-15/h1-8,18,22,24-25H,9-11,13-14H2,(H,23,26) checkY
    Key: YARKMNAWFIMDKV-UHFFFAOYSA-N checkY
  • C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
Properties
C20H23N3O4
Molar mass369.41432
Pharmacology
C07AB10 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Epanolol is abeta blocker.[1] developed byImperial Chemical Industries.[2]

Synthesis

[edit]

Theester methyl 4-benzyloxyphenylacetate (1) is treated withethylenediamine to give theamide (3). Separately, 2-cyanophenol (4) is reacted withepichlorohydrin andsodium hydroxide to produce thebenzonitrile derivative (5). Combination of (3) and (5) by heating inpropanol gives (6). Lastly, catalytic hydrogenation removes the benzylprotecting group and yields epanolol.[2][3]

See also

[edit]

References

[edit]
  1. ^Hosie, J.; Scott, A. K.; Petrie, J. C.; Cockshott, I. D. (1990)."Pharmacokinetics of epanolol after acute and chronic oral dosing in elderly patients with stable angina pectoris".British Journal of Clinical Pharmacology.29 (3):333–337.doi:10.1111/j.1365-2125.1990.tb03644.x.PMC 1380134.PMID 1968755.
  2. ^abLarge, M. S.; Smith, L. H. (1982). ".beta.-Adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido)alkyl]amino]-2-propanols".Journal of Medicinal Chemistry.25 (11):1286–1292.doi:10.1021/jm00353a004.PMID 6128420.
  3. ^"Epanolol". Thieme. Retrieved2024-06-30.
β, non-selective
β1-selective
β2-selective
α1- + β-selective
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