Carbamate derivatives of 2-arylimidazo[1,2-a]pyridinium salts as acetylcholinesterase inhibitors and protective agents against organophosphorus compounds.
A series of 2-arylimidazo[1,2-a]pyridinium salts with (N,N-dimethylcarbamoyl)oxy or (N-methylcarbamoyl)oxy groups at the 3'- or 4'-position on the phenyl substituent and various substituents on the imidazo[1,2-a]pyridine ring have been synthesized. The compounds show in vitro inhibitory activity against electric eel acetylcholinesterase (AChE), type III, and several of the compounds show protective effects toward the organophosphorus AChE inhibitor soman in mice. The possible structural relationship of these compounds to physostigmine and pyridostigmine is considered.
Department of Chemistry, University of Virginia, Charlottesville 22901.
R J
RJ
Sundberg
D
D
Dalvie
J
J
Cordero
H A
HA
Musallam
D000818:Animals; D000931:Antidotes / Q000138:chemical synthesis* / Q000494:pharmacology; D001285:Atropine / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D004557:Electric Organ / Q000201:enzymology; D004593:Electrophorus; D007928:Lethal Dose 50; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000037:antagonists & inhibitors / Q000633:toxicity*; D011220:Pralidoxime Compounds / Q000494:pharmacology; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D012999:Soman / Q000037:antagonists & inhibitors / Q000633:toxicity; D014961:X-Ray Diffraction
D000931:Antidotes; D002219:Carbamates; D002800:Cholinesterase Inhibitors; D009943:Organophosphorus Compounds; D011220:Pralidoxime Compounds; D011726:Pyridinium Compounds; D001285:Atropine; D012999:Soman