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

Victoria Richmond; Gustavo A Garrido Santos; Ana P Murray; Marta S Maier

doi:10.1016/j.steroids.2011.05.005

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

Steroids. 2011 Sep-Oct;76(10-11):1160-5. doi: 10.1016/j.steroids.2011.05.005. Epub 2011 May 27.

Authors

Victoria Richmond¹, Gustavo A Garrido Santos, Ana P Murray, Marta S Maier

Affiliation

¹ UMYMFOR (CONICET-UBA) and Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina.

PMID: 21640741
DOI: 10.1016/j.steroids.2011.05.005

Abstract

Disodium 2β,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 2β,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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylcholinesterase / metabolism*
Enzyme Activation / drug effects
Kinetics
Magnetic Resonance Spectroscopy
Steroids / chemical synthesis*
Steroids / chemistry
Steroids / pharmacology*

Substances

Steroids
Acetylcholinesterase