CODESSA-Based Theoretical QSPR Model for Hydantoin HPLC-RT Lipophilicities

Abstract

A quantitative structure property relationship investigation was performed on the lipophilicities of a number of hydantoin derivatives as measured by the RP-HPLC retention times provided by Scholl et al. (Scholl, S.; Koch, A.; Henning, D.; Kempter, G.; Kleinpeter, E. Struct. Chem. 1999, 10, 355-366). The lipophilicities (S) were correlated with the theoretical molecular descriptors of the hydantoins obtained using the CODESSA program from the AM1-optimized geometry and electron wave functions. This study discloses enhanced correlations of the lipophilicities with the molecular descriptors, wherein the influence of the entropy factor is found to predominate.

QSAR study for diarylguanidines, noncompetitive NMDA receptor antagonists. A new topological index AAd derived from local invariants of the chemical graphs of diarylguanidines

“…[32][33][34] For Table 1. In Figure 3 the experimental versus estimated log A data correlation is presented.…”

New N-aryloxy-phthalimide derivatives. Synthesis, physico-chemical properties, and QSPR studies

“…No satisfactory correlation for experimental λ max (Table 1) vs. calculated λ max was obtained using dipole moments plus net atomic charges (Table 1), but Eq. 7 allowed a fairly good correlation in terms of dipole moments D plus the average information content atomic index of order 0 (AIC 0 ) [39][40][41][42]; the average information content is defined on the basis of the Shannon information theory and is calculated as in formula I [41,42]. This is understandable because the dipole moment integrates information about the whole molecule, whereas net atomic charges on a single atom cannot provide such information.…”

“…Values for the calculated [39,40] R M0 in terms of ANRI C and HLB were obtained by Eq. 9: R M0 = -632.29 (±128.98) ANRI C -0.557 (±0.118) HLB + 12.11 (9) N = 8; R 2 = 0.889; SD = 0.536; R CV 2 = 0.791 Satisfactory correlations [39,40] (Eqs.…”

“…9: R M0 = -632.29 (±128.98) ANRI C -0.557 (±0.118) HLB + 12.11 (9) N = 8; R 2 = 0.889; SD = 0.536; R CV 2 = 0.791 Satisfactory correlations [39,40] (Eqs. 10 and 11) were found for R M0 :…”

QSAR for toxicities of polychlorodibenzofurans, polychlorodibenzo-1,4-dioxins, and polychlorobiphenyls

“…[80][81][82][83] Again, hundreds of molecular descriptors (structural, topological, quantum-chemical) are used and selected for the best correlation with a specified number of descriptors.…”