Epanolol

Epanolol is a beta blocker.[1]

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) N
    Key: YARKMNAWFIMDKV-UHFFFAOYSA-N N
  • InChI=1/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)
    Key: YARKMNAWFIMDKV-UHFFFAOYAY
  • C1=CC=C(C(=C1)C#N)OCC(CNCCNC(=O)CC2=CC=C(C=C2)O)O
Properties
C20H23N3O4
Molar mass 369.41432
Pharmacology
C07AB10 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

Amide-ester interchange between Methyl 4-benzyloxyphenylacetate [68641-16-7] (1) and ethylenediamine [107-15-3] (2) gives N-(2-aminoethyl)-2-(4-phenylmethoxyphenyl)acetamide, PC12841758 (3). The treatment of 2-Cyanophenol [611-20-1] (4) with epichlorohydrin in lye gives 2-glycidyloxybenzonitrile [38465-16-6] (5). Convergent synthesis between the two sections gives N-[2-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]ethyl]-2-(4-phenylmethoxyphenyl)acetamide, PC134990214 (6). Lastly, catalytic hydrogenation splits the benzyl protecting group completing the synthesis of Epanolol (7).

See also

References
  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. Pento, JT; Day, BW; Epanolol. Drugs Fut 1985, 10, 5, 392.
  3. Lare MS, Smith LH. Beta-adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido) alkyl]amino]-2-propanols. J Med Chem. 1982 Nov;25(11):1286-92. doi: 10.1021/jm00353a004. PMID: 6128420.
  4. Harold Smith Leslie, GB1573359 (1980 to Imperial Chemical Industries Ltd).
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