Synthesis and acetylcholinesterase inhibitory activity of 2ß,3α-disulfoxy-5α-cholestan-6-one.

Disodium 2ß,3α-dihydroxy-5α-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2ß,3α-dihydroxy-5α-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC(50) values of 14.59 and 59.65 µM, respectively. Diols 7 and 9 showed no inhibitory activity (IC(50)>500 µM).