Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes: synthesis and biological activity.
Six unsymmetrical bis-quaternary monooximes viz. dibromides of 1-(4-hydroxyiminomethyl pyridinium)-3-(3/4-carbamoyl pyridinium)propane, 1-(4-hydroxyiminomethyl pyridinium)-4-(3/4-carbamoyl pyridinium) butane, 1-(4-hydroxyiminomethyl pyridinium)-5-(3/4-carbamoyl pyridinium)pentane were synthesized and characterized by spectral data. Their ability to reactivate tetraethyl pyrophosphate inhibited mouse total brain cholinesterase was investigated and compared with 2-pyridine aldoxime chloride (2-PAM). All the compounds were found to be more effective acetylcholinesterase reactivators when compared with the conventional oxime, 2-PAM, except the compound (5a) with pentylene bridge and carbamoyl group present at fourth position. The bis-pyridinium monooximes with 3-carbamoyl group were more potent reactivators than the corresponding 4-carbamoyl compounds and bis-oximes tested.
Chennamaneni
Srinivas Rao
SR
Department of Pharmaceutics, University College of Pharmaceutical Sciences, Kakatiya University, Warangal 506 009 AP, India.
Vobalaboina
Venkateswarlu
V
Garlapati
Achaiah
A
D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism*; D000818:Animals; D001921:Brain / Q000187:drug effects / Q000201:enzymology; D002800:Cholinesterase Inhibitors / Q000494:pharmacology; D002801:Cholinesterase Reactivators / Q000138:chemical synthesis* / Q000494:pharmacology*; D004789:Enzyme Activation / Q000187:drug effects; D051379:Mice; D010091:Oximes / Q000138:chemical synthesis* / Q000494:pharmacology*; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D002800:Cholinesterase Inhibitors; D002801:Cholinesterase Reactivators; D010091:Oximes; D011726:Pyridinium Compounds; D000110:Acetylcholinesterase