A. Poso et al., BINDING OF SOME DIOXINS AND DIBENZOFURANS TO THE AH RECEPTOR - A QSARMODEL-BASED ON COMPARATIVE MOLECULAR-FIELD ANALYSIS (COMFA), Journal of molecular structure. Theochem, 101(3), 1993, pp. 259-264
Based on comparative molecular field analysis (CoMFA), a quantitative
structure-activity relationship, model for the cytosolic aryl hydrocar
bon (Ah) receptor binding affinity of 50 chlorinated dibenzo-para-diox
in and dibenzofuran analogues is presented. The electronic structures
of these compounds were calculated using the semiempirical AM 1 method
. Their extreme stabilities were rationalized using the frontier molec
ular orbital theory. The results indicate that their binding affinity
was mainly influenced by steric and electrostatic interactions, wherea
s charge-transfer and hydrogen bonding mechanisms are probably of mino
r importance.