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
CAS Number	66451-06-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1742431
PubChem CID	68863
UNII	66STS87GEY
CompTox Dashboard (EPA)	DTXSID401024384
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,7-12H2,1-2H3 Key: NACJSVRGPPMZRS-UHFFFAOYSA-N
SMILES CC(C)NCC(COC1=CC=CC=C1C2CC3CCC2C3)O
Properties
Chemical formula	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

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).