Journal of Medicinal Chemistry p. 822 - 824 (1985)
Update date:2022-08-03
Topics:
Oatis, John E.
Walle, T.
Daniell, H. B.
Gaffney, T. E.
Knapp, D. R.
4'-Hydroxypropranolol sulfate (8) was recently identified as a major metabolite of propranolol (Inderal).In order to confirm the structure and to further study disposition and biological activity, he have synthesized 8 with use of 1,4-naphthoquinone (1) as the starting material.Reduction and alkylation with benzyl iodide gave 4-(benzyloxy)naphthol (3).Sulfation and chlorosulfuric acid in N,N-dimethylaniline gave potassium 1-(benzyloxy)-4-naphthol sulfate (4).Catalytic hydrogenation, alkylation with <<<(trifluoromethyl)sulfonyl>oxy>methyl>oxirane (6), and amination in isopropylamine gave 8.Racemic 8 was found to be 100-1000 times less potent than racemic propranolol as a β-adrenergic receptor blocking agent in the dog.
View MoreContact:0086-29-88315623
Address:S711, Innovation Bldg No.25 Gaoxin 1st Rd, Xian P.R of China 710075
Contact:+86 021-51698675
Address:1701, Jielong Plaza, No.618 Pingliang Rd, ShangHai,China
Qingdao XinYongAn Chemicals Co., Ltd
Contact:+86-532-81107967
Address:Chengyang dual-port industrial park by the sea,Qingdao
Tianjin Anda North Industrial & Business Co.Ltd.
Contact:86-22-24999306
Address:No.11 Erwei Road,Dongli Development Area,Tianjin,China
Wuhan Jadechem International Trade Co.,Ltd.
website:http://www.jadechem-intl.com
Contact:+86-27-83527060
Address:Room 502,Building C11,Software new city No.8,Huacheng Avenue,East Lake High-tech development zone,Wuhan,Hubei,China
Doi:10.1002/jhet.5570210553
(1984)Doi:10.1016/S0040-4039(00)60066-7
(1993)Doi:10.1002/jhet.5570210550
(1984)Doi:10.1002/chem.200700866
(2008)Doi:10.1021/ja075277e
(2007)Doi:10.1055/s-1984-30968
(1984)