TY - JOUR
T1 - Synthesis and cytotoxic analysis of some disodium 3β,6β-dihydroxysterol disulfates
AU - Cui, Jianguo
AU - Wang, Hui
AU - Huang, Yanmin
AU - Xin, Yi
AU - Zhou, Aimin
N1 - Funding Information:
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.
Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.
PY - 2009/11
Y1 - 2009/11
N2 - 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.
AB - 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.
KW - Antineoplastic activity
KW - Biological activity
KW - Disodium 3β,6β-dihydroxysterol disulfates
KW - Synthesis
UR - http://www.scopus.com/inward/record.url?scp=70350567768&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=70350567768&partnerID=8YFLogxK
U2 - 10.1016/j.steroids.2009.08.006
DO - 10.1016/j.steroids.2009.08.006
M3 - Article
C2 - 19703482
AN - SCOPUS:70350567768
VL - 74
SP - 1057
EP - 1060
JO - Steroids
JF - Steroids
SN - 0039-128X
IS - 13-14
ER -