Decalin-type acetylcholine-mimetic organophosphates as inhibitors of acetylcholinesterase.
The novel decalin-type N,O,P-heterocycles, P(3)-axially and P(3)-equatorially substituted cis- and trans-configurated 3-fluoro-2,4-dioxa-7-aza-, 2,4-dioxa-8-aza-, and 2,4-dioxa-9-aza-3-phosphabicyclo[4.4.0]decane 3-oxides, are configuratively fixed and conformationally constrained phosphorus analogues of acetylcholine. The compounds are suitable probes for the investigation of molecular interactions with acetylcholinesterase.
Furegati
Stefan
S
Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
Gorla
Fabrizio
F
Linden
Anthony
A
Rüedi
Peter
P
D000109:Acetylcholine / Q000737:chemistry*; D000110:Acetylcholinesterase / Q000378:metabolism*; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D007700:Kinetics; D018716:Molecular Mimicry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry* / Q000494:pharmacology*; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D002800:Cholinesterase Inhibitors; D009281:Naphthalenes; D009943:Organophosphorus Compounds; C007229:decalin; D000110:Acetylcholinesterase; D000109:Acetylcholine