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Synthesis and anticholinesterasic activity of some α-thio-substituted O-(methylcarbamoyl)oximes

Vilarem, Gérard and Merlina, Georges and Calmon, Jean-Pierre Synthesis and anticholinesterasic activity of some α-thio-substituted O-(methylcarbamoyl)oximes. (1989) Journal of Agricultural and Food Chemistry, 37 (1). 173-177. ISSN 0021-8561

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Official URL: http://dx.doi.org/10.1021/jf00085a040


A series of six oxime N-methylcarbamates, C6H5C(R)=NOCONHCH3[ R = SCH3, CH2SCH3,( 2)-an d (E)-CH(CH),)SCH,, C(CH3)2SCH3C, (CH3),], analogues of commercial compounds such as aldicarb, butocarboxim, methomyl, and thiofanox, was synthesized for potential anticholinesterasic activity. NMR, IR, and UV were used to assign the configurations. The kinetic study of the inhibition of acetylcholinesterase from bovine erythrocyte and the determination of the dissociation constant Kd and of the carbamylation rate constant k2 allowed discussion of the importance of the number of methyl groups on the carbon a to the iminic group. The insertion of the phenyl group generally did not improve the activity but yielded compounds, one isomer of which had a potential activity close to that of the commercial compounds.

Item Type:Article
HAL Id:hal-03486851
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS (FRANCE)
Université de Toulouse > Institut National Polytechnique de Toulouse - Toulouse INP (FRANCE)
Université de Toulouse > Université Toulouse III - Paul Sabatier - UT3 (FRANCE)
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Deposited On:05 Apr 2013 07:24

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