Bornaprolol

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;
ChemSpider	62095;
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

Bornaprolol is a beta-adrenergic antagonist.^[1]

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

^ 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.
^ Michaud, R.; Bornaprolol hydrochloride. Drugs Fut 1982, 7, 2, 91.
^ Hardy, J.C. et al, Bull. Soc. Chim. Fr., Part 2, 1982, 304.
^ 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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[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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