QSPR/QSAR in N-[(dimethylamine)methyl] benzamides substituents groups influence upon electronic distribution and local anesthetics activity

Bioorg Med Chem. 2004 Mar 15;12(6):1377-81. doi: 10.1016/j.bmc.2004.01.011.

Abstract

It was determined, with a systematic mode, the carbonyl group frequency in the region of the infrared of N-[(dimethylamine)methyl] benzamides 4-substituted (set A) and their hydrochlorides (set B), that had its local anesthetical activity evaluated. The application of the Hammett equation considering the values of the absorption frequency of carbonyl group, nu(C=O,) using the electronic constants sigma, sigma(I), sigma(R), I and R leads to meaningful correlation. The nature and the contribution of substituent group electronic effects on the polarity of the carbonyl group was also analyzed. The use of the nu(C=O) as an experimental electronic parameter for QSPR studies was validated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anesthetics, Local / pharmacology*
  • Animals
  • Benzamides / pharmacology*
  • Central Nervous System / drug effects*
  • Central Nervous System / metabolism
  • Dimethylamines / pharmacology*
  • Electrons*
  • Molecular Structure
  • Quantitative Structure-Activity Relationship
  • Rats
  • Rats, Wistar

Substances

  • Anesthetics, Local
  • Benzamides
  • Dimethylamines
  • dimethylamine