Synthesis of dihydroxanthone derivatives and evaluation of their inhibitory activity against acetylcholinesterase: unique structural analogs of tacrine based on the BCD-ring of arisugacin

S J Degen; K L Mueller; H C Shen; J A Mulder; G M Golding; L L Wei; C A Zificsak; A Neeno-Eckwall; R P Hsung

doi:10.1016/s0960-894x(99)00115-8

Synthesis of dihydroxanthone derivatives and evaluation of their inhibitory activity against acetylcholinesterase: unique structural analogs of tacrine based on the BCD-ring of arisugacin

Bioorg Med Chem Lett. 1999 Apr 5;9(7):973-8. doi: 10.1016/s0960-894x(99)00115-8.

Authors

S J Degen¹, K L Mueller, H C Shen, J A Mulder, G M Golding, L L Wei, C A Zificsak, A Neeno-Eckwall, R P Hsung

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.

PMID: 10230623
DOI: 10.1016/s0960-894x(99)00115-8

Abstract

A general approach to synthesis of dihydroxanthone derivatives is described here. In vitro evaluation of these dihydroxanthones demonstrated that some derivatives possess moderate anti-cholinesterase activities and better selectivities than tacrine for acetylcholinesterase over butyrylcholinesterase. Structural effects on anti-cholinesterase activities were also examined, and docking experiments were carried out to provide preliminary understandings of these experimental observations.

Publication types

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

MeSH terms

Acetylcholinesterase / drug effects*
Cholinesterase Inhibitors / chemistry
Cholinesterase Inhibitors / pharmacology*
Molecular Structure
Pyrans / chemistry*
Tacrine / chemistry
Tacrine / pharmacology*

Substances

Cholinesterase Inhibitors
Pyrans
arisugacin
Tacrine
Acetylcholinesterase