Journal of Medicinal Chemistry p. 1690 - 1701 (1984)
Update date:2022-08-04
Topics:
Rasmusson, Gary H.
Reynolds, Glenn F.
Utne, Torleif
Jobson, Ronald B.
Primka, Raymond L.
et al.
A series of A-ring heterocyclic steroids has been prepared and tested for inhibition of rat prostatic steroid 5α-reductase in vitro.Strinkingly high inhibitory activity was found with a group of 17β-substituted 4-methyl-4-aza-5α-androstan-3-ones.These compounds were prepared from 3-keto-Δ4-precursors by oxidative (O3 or NaIO4-KMnO4) A-ring cleavage followed, in turn, by ring closure with an amine and hydrogenation over platinum catalyst.Other A-ring azasteroids were made by Beckmann rearrangement of oximes of 2-oxo-A-nor-, 3-oxo- and 4-oxo-5α-androstanes.An A-nor-2-oxo-3-azasteroid was prepared by oxidative decarbonylation of a precursor 2,3-dioxo-4-azasteroid with m-chloroperbenzoic acid.A-ring modifications of the 4-azasteroids included Δ1-unsaturation, 2- and 4-substituents, and 3-carbonyl replacements.Side chains at the 17-position were varied with an emphasis on carboxylate derivatives (salts, esters, and amides).
View MoreSuzhou Wedo Chemicals Co., Ltd.
Contact:86 512 58100425
Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Hangzhou Dingyan Chem Co., Ltd
website:http://www.dingyanchem.com
Contact:86-571-87157530-8007
Address:RM.1118,NO.1 Building, Baiyun Tower,Jianggan Area, Hangzhou city, China,310004
Zhejiang Sanmei Chemical Industry Co., Ltd
Contact:86-579-87633213
Address:Huchu Industrial Zone, Qingnian Rd., Wuyi County, Zhejiang Prov., China.
Anhui Redstar Pharmaceutical Corp., Ltd
Contact:+86-563-5120837
Address:Jingxian Industrial Development Zone, Anhui , China
Contact:+86-22-26358246
Address:601-4-20, Fujiayuan, Tiantai Road, Hebei District, Tianjin, China
Doi:10.1021/ja804233g
(2008)Doi:10.1021/jo00376a050
(1986)Doi:10.1021/jo01284a002
(1967)Doi:10.1002/anie.202015246
(2021)Doi:10.1246/bcsj.38.378
(1965)Doi:10.1021/jm00239a005
(1975)