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Chemistry Faculty Publications
6β-dihydroxysterol disulfates; Synthesis; Biological activity; Antineoplastic activity
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Full-Text Articles in Physical Sciences and Mathematics
Synthesis And Cytotoxic Analysis Of Some Disodium 3Β,6Β-Dihydroxysterol Disulfates, Jianguo Cui, Hui Wang, Yi Xin, Aimin Zhou
Synthesis And Cytotoxic Analysis Of Some Disodium 3Β,6Β-Dihydroxysterol Disulfates, Jianguo Cui, Hui Wang, Yi Xin, Aimin Zhou
Chemistry Faculty Publications
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 …