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Bornaprolol

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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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Bornaprolol is abeta-adrenergic antagonist.^[1]

Synthesis

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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

[edit]

^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).