QSAR of aromatic substances: Toxicity of polychlorodibenzofurans

被引：5

作者：

Clare, BW ^{[1
]}

机构：

[1] Univ Western Australia, Sch Biomed & Chem Sci, Nedlands, WA 6009, Australia

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2006年 / 763卷 / 1-3期

关键词：

aromatic; QSAR; flip-regression; orbital nodes; polychlorodibenzofuran;

D O I：

10.1016/j.theochem.2006.01.023

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The flip regression procedure for handling substituted symmetric congeners described previously with regard to benzenoid aromatics has been applied to the dibenzofuran system that has similar symmetry. Polychlorodibetizofurans are important, highly toxic environmental contaminants that bind to the aryl hydrocarbon receptor (AhR). Their toxicity is known to correlate with their Pearson-Parr softness, and in this contribution it is shown that the orientation of nodes in their occupied pi orbitals explains a further large portion of the variance in their toxicity, the two together accounting for up to 95% of this variance. (c) 2006 Elsevier B.V. All rights reserved.

引用

页码：205 / 213

页数：9

共 21 条

[1] Structure-activity relationships for the toxicity of polychlorinated dibenzofurans: Approach through density functional theory-based descriptors [J].

Arulmozhiraja, S ;

Morita, M .

CHEMICAL RESEARCH IN TOXICOLOGY, 2004, 17 (03) :348-356

[2] Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model [J].

Barone, V ;

Cossi, M .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) :1995-2001

[3] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[4]

*BIOBYTE CORP, CLOGP WIND VERS 1 0

[5]

CLAR BW, NODANGLE ZIP VERS 2

[6] The frontier orbital phase angles: a theoretical interpretation [J].

Clare, BW .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2000, 507 :157-164

[7] Predictive flip regression: A technique for QSAR of derivatives of symmetric molecules [J].

Clare, BW ;

Supuran, CT .

JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2005, 45 (05) :1385-1391

[8] A physically interpretable quantum-theoretic QSAR for some carbonic anhydrase inhibitors with diverse aromatic rings, obtained by a new QSAR procedure [J].

Clare, BW ;

Supuran, CT .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (06) :2197-2211

[9] A novel quantum theoretic QSAR for hallucinogenic tryptamines:: a major factor is the orientation of π orbital nodes [J].

Clare, BW .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2004, 712 (1-3) :143-148

[10] QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens [J].

Clare, BW .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2002, 16 (8-9) :611-633

← 1 2 3 →