Bornaprolol

Bornaprolol is a beta-adrenergic antagonist.[1]

Bornaprolol
Names
IUPAC name
1-[2-(3-Bicyclo[2.2.1]heptanyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol
Identifiers
3D model (JSmol)
ChEMBL
UNII
  • InChI=1S/C19H29NO2/c1-13(2)20-11-16(21)12-22-19-6-4-3-5-17(19)18-10-14-7-8-15(18)9-14/h3-6,13-16,18,20-21H,7-12H2,1-2H3
    Key: NACJSVRGPPMZRS-UHFFFAOYSA-N
  • CC(C)NCC(COC1=CC=CC=C1C2CC3CCC2C3)O
Properties
C19H29NO2
Molar mass 303.446 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

The reaction between 2-(Bicyclo[2.2.1]hept-2-yl)phenol [17152-43-1] (1) and epichlorohydrin [106-89-8] (2) in the presence of sodium metal gives (3). Opening of the oxirane by treatment with isopropylamine [75-31-0] (4) completed the synthesis of Bornaprolol (5).

References
  1. Cheymol, G; Jaillon, P; Lecoq, B; Lecoq, V; Cheymol, A; Krumenacker, M (1987). "Cardiovascular beta-adrenergic blocking effects of bornaprolol in humans: Relation to dose and plasma concentration". Journal of Cardiovascular Pharmacology. 9 (6): 694–8. doi:10.1097/00005344-198706000-00009. PMID 2442536. S2CID 38782602.
  2. Michaud, R.; Bornaprolol hydrochloride. Drugs Fut 1982, 7, 2, 91.
  3. Hardy, J.C. et al, Bull. Soc. Chim. Fr., Part 2, 1982, 304.
  4. DE2735570 idem Jean Mardiguian, U.S. patent 4,157,400 (1985 to Marpha Societe D'etudes Et D'exploitation De Marques S.A., Paris, Fr).


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