Document Type
Article
Publication Date
12-1-2009
Publication Title
Steroids
Abstract
Disodium 3β,6β-dihydroxy-5α-cholestane disulfate (1) was synthesized in 4 steps with a high overall yield from cholesterol. First, cholesterol (4a) was converted to cholest-4-en-3,6-dione (5a) via oxidation with pyridinium chlorochromate (PCC) and then 5a was reduced by NaBH4 in the presence of NiCl2 to produce cholest-3β,6β-diol (6a). The reaction of 6a with the triethylamine-sulfur trioxide complex generated diammonium 3β,6β-dihydroxy-5α-cholestane disulfate (7a) and the treatment of 7a by cation exchange resin 732 (sodium form)(Na+) yielded the target steroid 1. Disodium 24-ethyl-3β,6β-dihydroxycholest-22-ene disulfate (2) and disodium 24-ethyl-3β,6β-dihydroxycholestane disulfate (3) were synthesized using a similar method. The cytotoxicity of these 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 was investigated. Our results indicate that presence of a cholesterol-type side chain at position 17 is necessary for their biological activity.
Recommended Citation
Cui, Jianguo; Wang, Hui; Xin, Yi; and Zhou, Aimin, "Synthesis and Cytotoxic Analysis of Some Disodium 3β,6β-Dihydroxysterol Disulfates" (2009). Chemistry Faculty Publications. 414.
https://engagedscholarship.csuohio.edu/scichem_facpub/414
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.2009.08.006
Version
Postprint
Volume
74
Issue
13-14
Comments
The authors acknowledge the financial support of the National Natural Science Foundation of China (No.: 20562001), the Natural Science Foundation of Guangxi Province (No.: 0575054) of China.