Structure—Activity Correlations of Selected Azaarenes, Aromatic Amines, and Nitroaromatics

Abstract

Quantitative chemical structure — biological activity relationships between the molecular descriptors 1-octanol/water partition coefficient (log Kow), the 1Xv (one-chi-V) molecular connectivity index and (log Kow)2 and the biological response measured as population growth impairment to the ciliate Tetrahymena pyriformis were investigated for a series of 21 nitrogen substituted aromatic molecules. The test molecules included seven each of the azaarenes, primary aromatic amines and nitroaromatics including single, double and triple ring compounds. Nitro-containing homologs are the most active followed by amino-containing ones and azaarenes. Within each analog series activity increases with alkyl substitution and ring addition. The QSAR model: log BR = 0.8255(log Kow) - 1.6334 was determined to be an excellent predictive model which accounted for 86.9% of the variability in the observed biological activity. This model is thought to express non-specific toxicity due to membrane perturbation.