Synthesis and in vitro anticholinesterase activity of a series of oxime N-methylcarbamates. Structure-activity relationships
1992
Saad, M. | Mrlina, G. | Calmon, J.P.
A series of 33 oxime N-methylcarbamates R1R2C=NOCONHCH3 [R1 and R2 = H, alkyl, cycloalkyl, halodkyl, substituted aryl, or groups like (CH3)2C=CH, CF3COCH2] was synthesized and tested for potential anticholinesterase activity. Some of those compounds such as the alpha,alpha,alpha-trifluoroacetophenoxime derivatives were studied for their in vitro and in vivo activity; other structures are novel ones. The configuration of those compounds was assigned by spectroscopic methods (NMR, IR, UV). The measure of the residual activity of the acetylcholinesterase (bovine erythrocyte) after the inhibition by those molecules allowed the determination of the dissociation constant Kd and the bimolecular carbamoylation rate constant ki. To take isomerism into account, the group R2 is always cis to the carbamic moiety. The structure-activity relationship studies were performed with the usual structural parameters and included commercial compounds such as aldicarb, methomyl, and oxamyl. The correlation equation obtained is (...). Specific correlations exhibit the prevailing participation of the group R2 in the formation of the enzyme-inhibitor complex and in the interactions of the inhibitor with the trimethyl site.
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