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Bornaprolol

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Bornaprolol
Names
IUPAC name 1-heptanyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,7-12H2,1-2H3Key: NACJSVRGPPMZRS-UHFFFAOYSA-N
SMILES
  • CC(C)NCC(COC1=CC=CC=C1C2CC3CCC2C3)O
Properties
Chemical formula C19H29NO2
Molar mass 303.446 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bornaprolol is a beta-adrenergic antagonist.

Synthesis

ChemDrug Synthesis: Patent:

The reaction between 2-(Bicyclohept-2-yl)phenol (1) and epichlorohydrin (2) in the presence of sodium metal gives (3). Opening of the oxirane by treatment with isopropylamine (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).


Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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