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ID: ALA3046800

Journal: Bioorg Med Chem

Title: Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors.

Authors: Finkelstein BL, Benner EA, Hendrixson MC, Kranis KT, Rauh JJ, Sethuraman MR, McCann SF.

Abstract: Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH(2)) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC(50) values comparable to the organophosphate Paraoxon. Unlike organophosphates, cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A.

CiteXplore: 11814848

DOI: 10.1016/s0968-0896(01)00326-1