Epanolol

Epanolol
Names

IUPAC name (RS)-N-[2-([3-(2-cyanophenoxy)-2-hydroxypropyl]amino)ethyl]-2-(4-hydroxyphenyl)acetamide
Identifiers
CAS Number	86880-51-5^Y
3D model (JSmol)	Interactive image
ChemSpider	65013^Y
KEGG	D06646^Y
PubChem CID	72014
UNII	9KGC55KP6A^Y
CompTox Dashboard (EPA)	DTXSID90868959
InChI 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)^Y Key: YARKMNAWFIMDKV-UHFFFAOYSA-N^Y
SMILES C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
Properties
Chemical formula	C₂₀H₂₃N₃O₄
Molar mass	369.41432
Pharmacology
ATC code	C07AB10 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Epanolol is a beta blocker.^[1] developed by Imperial Chemical Industries.^[2]

Synthesis

The ester methyl 4-benzyloxyphenylacetate (1) is treated with ethylenediamine to give the amide (3). Separately, 2-cyanophenol (4) is reacted with epichlorohydrin and sodium hydroxide to produce the benzonitrile derivative (5). Combination of (3) and (5) by heating in propanol gives (6). Lastly, catalytic hydrogenation removes the benzyl protecting group and yields epanolol.^[2]^[3]

References

^ 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.
^ ^a ^b Large, 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.
^ "Epanolol". Thieme. Retrieved 2024-06-30.