Bornaprolol

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
ChemSpider
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).

Bornaprolol is a beta-adrenergic antagonist.[1]

Synthesis

ChemDrug Synthesis:[2][3] Patent:[4]

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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