The use of substituent constants in the study of structure-activity relationships in cholinesterase inhibitors

Hansch, Corwin; Deutsch, Edna W.

doi:10.1016/0926-6585(66)90042-2

Cited by 103 publications

(47 citation statements)

References 24 publications

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“…3 J P-C , 2 J P-C but in cyclic group N(CH 2 ) 4 O, 2 J P-C , 3 J P-C which is in agreement with the previous results about cyclic and acyclic amines linked to phosphorus atom [13].…”

Section: Synthesis and Spectral Datasupporting

confidence: 82%

“…(1) Intramolecular properties such as lipophilicity, electronic, refractory, steric and topological properties [4], that steer the insecticide through the 'gorge' and participate in their binding to the active center. (2) Three-dimensional structure of OPs that provide positioning of the leaving group in the enzyme's active center [5], thus facilitating phosphorylation.…”

Section: Introductionmentioning

confidence: 99%

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Structure-activity study of phosphoramido acid esters as acetylcholinesterasf inhibitors

Ghadimi

Valmoozi

Pourayoubi

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…3 J P-C , 2 J P-C but in cyclic group N(CH 2 ) 4 O, 2 J P-C , 3 J P-C which is in agreement with the previous results about cyclic and acyclic amines linked to phosphorus atom [13].…”

Section: Synthesis and Spectral Datasupporting

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Structure-activity study of phosphoramido acid esters as acetylcholinesterasf inhibitors

Ghadimi

Valmoozi

Pourayoubi

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The plot reveals the influence of steric effects in the inhibition of AChE by these compounds, i.e., the inhibition rates are reduced as the alkyl moiety attached to the phosphorus atom becomes bulkier. The importance of steric effects in AChE inhibition was subsequently pointed out by Hansch and Deutsch (13) who showed that anticholinesterase activities for the compounds in Figure 5 were related to Taft's steric substituent constant, E., cyi -Ch3H7 cyclohexyl alkylphosphonate esters, it also revealed that the Palkyl moiety should be kept small (methyl or ethyl) in designing potential insecticides from phosphonate esters.…”

Section: Mechanism Of Inhibitionmentioning

confidence: 99%

Mechanism of Action of Organophosphorus and Carbamate Insecticides

Fukuto¹

1990

Environmental Health Perspectives

206

255

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Organophosphorus and carbamate insecticides are toxic to insects and mammals by virtue of their ability to inactivate the enzyme acetylcholinesterase. This review addresses the mechanism of inhibition of acetylcholinesterase by organophosphorus and carbamate esters, focusing on structural requirements necessary for anticholinesterase activity. The inhibition of acetylcholinesterase by these compounds is discussed in terms of reactivity and steric effects. The role of metabolic activation or degradation in the overall intoxication process is also discussed.

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“…In a series of papers which represent the most important advance in the quantification of biological activities up to the present time Hansch and his co-workers (11)(12)(13)(14) found that an equation of the form BAx = PUx + Svx + T,Tx + T2T2X + h (8) is generally applicable to biological activities. p, S, T1, T2 and h are coefficients determined by correlating some data set of interest with Eq.…”

Section: Transport Parametersmentioning

confidence: 99%

Some methods of obtaining quantitative structure-activity relationships for quantities of environmental interest.

Charton¹

1985

Environ Health Perspect

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Methods are described for obtaining quantitative structure-activity relationships (QSAR) for the estimation of quantities of environmental interest. Toxicities of alkylamines and of alkyl alkanoates are well correlated by the alkyl bioactivity branching equation (ABB). Narcotic activities of 1,1-disubstituted ethylenes are correlated by the intermolecular forces bioactivity (IMF) equation. When the data set has a limited number of substituents in equivalent positions the group number (GN) equation, derivable from the IMF equation, can be used for correlation. It has been successfully applied to aqueous solubilities, 1-octanol-water partition coefficients, and bioaccumulation factors and ecological magnifications for organochlorine compounds. A combination of the omega method for combining data sets for different organisms with the GN equation has been used to correlate toxicities of organochlorine insecticides in two species of fish. Toxicities of carbamates have been correlated by a combination of the zeta method and the IMFB equation. The ABB and the GN equations are particularly useful in that they generally do not require parameter tables, and that the parameters they use are error-free. The methods presented here, as shown by the examples given, should make it possible to establish a collection of QSAR for toxicities, bioaccumulation factors, aqueous solubilities, partition coefficients, and other properties of sets of compounds of environmental interest.

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The use of substituent constants in the study of structure-activity relationships in cholinesterase inhibitors

Cited by 103 publications

References 24 publications

Structure-activity study of phosphoramido acid esters as acetylcholinesterasf inhibitors

Structure-activity study of phosphoramido acid esters as acetylcholinesterasf inhibitors

Mechanism of Action of Organophosphorus and Carbamate Insecticides

Some methods of obtaining quantitative structure-activity relationships for quantities of environmental interest.

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