Physicochemical parameters involved in the lethal toxicity of N,N-[(dimethylamino)ethyl]-4-substituted benzoate hydrochlorides: A QSAR study
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Data
1997-01-01
Autores
doAmaral, A. T.
Oliveira, A. C.
Neidlein, R.
Gallacci, M.
Caprara, L.
Miyazaki, Y.
Título da Revista
ISSN da Revista
Título de Volume
Editor
Elsevier B.V.
Resumo
A set of sixteen para-substituted N,N-[(dimethylamino)ethyl] benzoate hydrochlorides structurally related to procaine was synthesized. The apparent partition coefficients were determined by either shake-flask or HPLC methods and were taken as hydrophobic parameters. The IR stretching frequencies of the carbonyl group were determined in chloroform and taken as one of the electronic parameters. Additional physicochemical parameters were either taken from the literature: pi, sigma, T and R, MR4, or calculated: log P. The lethal potency was determined in the mouse via the LD50. In order to verify the nature and the relative contributions of the physicochemical parameters to lethal toxicity, QSAR equations were derived using regression analysis. A major contribution of hydrophobicity to ether with a smaller but still significant contribution of electronic or polar properties was found to a describe the toxicity within this set of compounds.
Descrição
Palavras-chave
physicochemical parameters, hydrophobicity, para-substituted N,N-[(dimethylamino)ethyl]benzoate hydrochlorides, lethal toxicity, QSAR
Como citar
European Journal of Medicinal Chemistry. Paris: Editions Scientifiques Medicales Elsevier, v. 32, n. 5, p. 433-443, 1997.