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Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity.
A review of the literature yielded data on over 200 aromatic and heteroaromatic nitro compounds tested for mutagenicity in the Ames test and a quantitative structure-activity relationship (QSAR) has been derived for 188 congeners, showing that chemicals possessing three or more fused rings possess much greater mutagenic potency than compounds with one or two fused rings.
The relative toxicity of compounds in mainstream cigarette smoke condensate.
  • C. Smith, C. Hansch
  • Chemistry, Medicine
    Food and chemical toxicology : an international…
  • 1 July 2000
Rank ordered some of the important compounds in cigarette smoke condensate by their measured or potential toxicity, since it affects metabolism, biological transport properties and intrinsic toxicity.
Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design.
The principle is proposed that drugs should be made as hydrophilic as possible without loss of efficacy, and Antihistamines are discussed in terms of what kind of hydrophobic-hydrophilic balance is best to avoid CNS-related problems.
A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100
Mutagenic activity in TA98 is also found to depend on the size of the aromatic ring system, and the mechanism of amine activation and reaction with DNA is considered in light of these findings.
Lipophilic character and biological activity of drugs. II. The parabolic case.
The analyses in this review are all based on the operational definition of lipophilic character by log P from the octanol-water system, which is, of course, great advantage in using a single reference system.
IARC carcinogens reported in cigarette mainstream smoke and their calculated log P values.
The list of IARC classified carcinogens from 68 to 81 compounds is expanded and Lipophilicity, as determined by the base 10 logarithm of the calculated octanol-water partition coefficient and denoted as Clog P, is reported for each of the 71 non-metallic MS IARC carcinogens.
Thiopurine methyltransferase. Aromatic thiol substrates and inhibition by benzoic acid derivatives.
"aryl thiol methyltransferase" might be a better name than "thiopurine methyl transferase" for this enzyme, after several nonheterocyclic aromatic thiol compounds, including thiophenol and thiosalicylic acid, were discovered to be substrates for TPMT.
Percutaneous penetration of para-substituted phenols in vitro.
The quadratic log Jmax correlation with log P was compared to the previously reported steady-state permeability coefficients (Kp) of a different set of phenol analogs through human epidermis, and suggest that the form of this correlation may be suitable description of Phenol permeability under a range of experimental conditions.
Mutagenicity of quinolines in Salmonella typhimurium TA100. A QSAR study based on hydrophobicity and molecular orbital determinants.
Quantitative structure-activity relationships (QSAR) could be formulated using molecular orbital parameters or Hammett constants and hydrophobic parameters for those compounds with substituents in the 6, 7 and 8 positions and points to the 2-position on the quinoline ring as being the site for activation by S9 oxidation.