Bunitrolol

Bunitrolol
Names
IUPAC name
2-[3-(tert-Butylamino)-2-hydroxypropoxy]benzonitrile
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3
    Key: VCVQSRCYSKKPBA-UHFFFAOYSA-N
  • InChI=1/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3
    Key: VCVQSRCYSKKPBA-UHFFFAOYAU
  • CC(C)(C)NCC(COC1=CC=CC=C1C#N)O
Properties
C14H20N2O2
Molar mass 248.326 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bunitrolol is a beta-adrenergic antagonist.[1]

Synthesis

2-Hydroxybenzonitrile (1) is treated with epichlorohydrin and sodium hydroxide to give the epoxide (2). Addition of tert-butylamine completes the synthesis of bunitrolol.[2]

See also

References

  1. ^ Haddad, S; Poulin, P; Funk, C (2010). "Extrapolating in vitro metabolic interactions to isolated perfused liver: Predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine". Journal of Pharmaceutical Sciences. 99 (10): 4406–26. doi:10.1002/jps.22136. PMID 20310018.
  2. ^ Herbert Koppe, Albrecht Engelhardt, Karl Zeile, U.S. patent 3,940,489 (1976 to Boehringer Ingelheim Gmbh).
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