Epanolol
{{chembox
| ImageFile=Epanolol.svg
| IUPACName=(RS)-N-[2-([3-(2-cyanophenoxy)-2-hydroxypropyl]amino)ethyl]-2-(4-hydroxyphenyl)acetamide
| OtherNames=
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9KGC55KP6A
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=86880-51-5
| PubChem=72014
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06646
| SMILES=C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 65013
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YARKMNAWFIMDKV-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula=C20H23N3O4
| MolarMass=369.41432
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
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|Section6={{Chembox Pharmacology
| ATCCode_prefix = C07
| ATCCode_suffix = AB10
}}
|Section7={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
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Epanolol is a beta blocker.{{Cite journal | last1 = Hosie | first1 = J. | last2 = Scott | first2 = A. K. | last3 = Petrie | first3 = J. C. | last4 = Cockshott | first4 = I. D. | title = Pharmacokinetics of epanolol after acute and chronic oral dosing in elderly patients with stable angina pectoris | journal = British Journal of Clinical Pharmacology | volume = 29 | issue = 3 | pages = 333–337 | year = 1990 | pmid = 1968755 | pmc = 1380134 | doi=10.1111/j.1365-2125.1990.tb03644.x }} developed by Imperial Chemical Industries.{{cite journal |doi=10.1021/jm00353a004 |title=.beta.-Adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido)alkyl]amino]-2-propanols |date=1982 |last1=Large |first1=M. S. |last2=Smith |first2=L. H. |journal=Journal of Medicinal Chemistry |volume=25 |issue=11 |pages=1286–1292 |pmid=6128420 }}
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.{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0027 |title=Epanolol |publisher=Thieme |access-date=2024-06-30}}
See also
References
{{reflist}}
{{Beta blockers}}
Category:4-Hydroxyphenyl compounds
Category:Phenoxypropanolamines
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