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Butofilolol

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Butofilolol
Clinical data

Other names	CM-6805
ATC code	none
Identifiers
IUPAC name (RS)-1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-fluorophenyl]butan-1-one
CAS Number	58930-32-8^Y
PubChemCID	68838
ChemSpider	62071^Y
UNII	4AZC6Y5A8G
ChEMBL	ChEMBL157443^Y
CompTox Dashboard(EPA)	DTXSID30867082
ECHA InfoCard	100.055.892
Chemical and physical data
Formula	C₁₇H₂₆FNO₃
Molar mass	311.397 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Fc1ccc(OCC(O)CNC(C)(C)C)c(c1)C(=O)CCC
InChI InChI=1S/C17H26FNO3/c1-5-6-15(21)14-9-12(18)7-8-16(14)22-11-13(20)10-19-17(2,3)4/h7-9,13,19-20H,5-6,10-11H2,1-4H3^Y Key:NMBNQRJDEPOXCP-UHFFFAOYSA-N^Y

Butofilolol (trade nameCafide) is abeta-blocker drug for the treatment ofessential hypertension (high blood pressure).^[1]^[2] It is not known to be marketed anywhere.

It is an example of abutyrophenone.

Synthesis

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TheFries rearrangement of theester formed by 4-fluorophenol (1)^[3] and butryryl chloride (2) gives 5'-fluoro-2'-hydroxybutyrophenone (3). Treatment withepichlorohydrin in the presence of base leads to 1-[5-fluoro-2-(oxiranylmethoxy)phenyl]butan-1-one (4). Lastly, reaction withtert-butylamine gives butofilolol.^[4]^[5]

References

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^Houin G, Barre J, Jeanniot JP, Ledudal P, Cautreels W, Tillement JP (1984). "Pharmacokinetics of butofilolol (CAFIDE) after repeated oral administration in man".International Journal of Clinical Pharmacology Research.4 (3):175–83.PMID 6149195.
^Toussain P, Gay G, Debry G (June 1983). "[Long-term hypotensive treatment by butofilolol]".Annales de Cardiologie et d'Angeiologie.32 (4):277–83.PMID 6412614.
^Mercier C, Youmans P (1996). "4-fluorophenol: A key intermediate for agrochemicals and pharmaceuticals".The Roots of Organic Development. Industrial Chemistry Library. Vol. 8. pp. 293–300.doi:10.1016/S0926-9614(96)80020-7.ISBN 978-0-444-82434-9.
^Castañer J, Neuman M (1982). "Butofilolol".Drugs of the Future.7 (2): 96.doi:10.1358/dof.1982.007.02.199366.
^US 4252825, Demarne H, "ompositions for treatment of cardiovascular conditions associated with overproduction of catecholamines", issued 24 February 1981, assigned to C. M. Industries )