Efeitos de substituintes sobre a polaridade do grupo carbonila e a atividade anestésica local de N.N - [(dimetilamino) metil benzamidas para substituídas / Effect of substituents on carbonyl group polarity and local anesthetic activity of N,N-[(dimethyamine)methyl]benzhidrazides-para-substituted

AUTOR(ES)

Leoberto Costa Tavares

FONTE

IBICT - Instituto Brasileiro de Informação em Ciência e Tecnologia

DATA DE PUBLICAÇÃO

22/12/1987

RESUMO

In the present work nine N,N-[(dimethyl amino)methyl]benzamides-p-X-substituededs hydrochlorides (SERIES II) were prepared from the corresponding bases, (SERIES I), where X = N02, Br, Cl, I, F, H, CH3, OCH3 and N(CH3)3. The purity of the novel compounds, SERIES II, was established by elemental analysis. The recorded infrared and 1HNMR spectra were in agreement with their structures. For both sets of compounds the carbonyl group infrared frequencies in HCCl3 were determined and used as measurement of the polarity of the group. The obtained vC=O (cm-1) values showed excellent correlations when a simple or a multiparameter HAMMETT equation was applied. This suggests that the eletronic effect of the substituents on the carbonyl stretching frequencies is of inductive and ressonanee nature, without predominances of one over the other. Were also determined by peripheryc nervous blockade on rats paw, the degree of local anesthetic activity on seven of the nine compounds of SERIES II. The application of the HANSCH equation to the local anesthetie activity values showed reasonable correlation when the eletronic and hydrophobic effects of the substituents were considered. Analysis of the obtained regression coefficents suggest that the contribution of the former effect to the local anesthetic activity predominants.

ASSUNTO(S)

análise de hansch anestésicos locais carbonyl group grupo carbonila hansch analysis local anesthetic polaridade polarity quantitative structure-activity relationships - qsar relações quantitativas entre estrutura química e atividade biológica - qsar

Documentos Relacionados

• Substituent effect on carbonyc sthretching of esters frequencies
• Efeitos de substituintes em ésteres de ácido e delta sobre a polaridade de carbonila e a velocidade lactonização
• Photophysical properties of aromatic substituents in N-metil-1,8-naftalimida derivatives: correlation between theoretical and experimental data
• Grupos satisfazendo as condições (A,n) e (N,n)
• AVALIAÇÃO DO POTENCIAL ANTINOCICEPTIVO DE NOVOS 3- METIL-1H-1-PIRAZOL METIL ESTERES 5-SUBSTITUÍDOS EM CAMUNDONGOS