Document Type
Article
Publication Date
3-1-2008
Publication Title
Steroids
Abstract
Using β-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, β-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6a) via oxidation with pyridinium chlorochromate (PCC). Selective reduction of 6a by NaBH4 in the presence of CoCl2 gives 24-ethylcholest- 4-en-3β-ol-6-one (7a). The reaction of 7a with hydroxylamine hydrochloride offers the oxime 8a and the oxidation of 8a by Jones reagent gives the target steroid 1. (6E)-Hydroximinocholest-4-en-3-one (2) and (6E)-hydroximino-24-ethylcholest-4,22-dien-3-one (4) were synthesized by a similar method. The cytotoxicity of the synthesized compounds against sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells were investigated. The presence of a cholesterol-type side chain appears to be necessary for the biological activity.
Recommended Citation
Cui, Jianguo; Huang, Liliang; Fan, Lei; and Zhou, Aimin, "A Facile and Efficient Synthesis of Some (6E)-Hydroximino-4-En-3-One Steroids, Steroidal Oximes From Cinachyrella spp. Sponges" (2008). Chemistry Faculty Publications. 374.
https://engagedscholarship.csuohio.edu/scichem_facpub/374
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
DOI
10.1016/j.steroids.2007.10.007
Version
Postprint
Volume
73
Issue
3
Comments
The authors acknowledge the financial support of the National Natural Science Foundation of China (Project: 20562001), the Natural Science Foundation of Guangxi Province (Guike: 057554) and the graduate innovation fund of Guangxi Province.