Quantitative Models of Steric Effects

Unger, Stefan; Hansch, Corwin

doi:10.1002/9780470171912.ch4

Cited by 174 publications

(32 citation statements)

References 128 publications

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“…41 For drugs acting as LO inhibitors, hydrophobicity is an important property, it is also a significant factor in the susceptibility of drugs to attack by the P-450 enzymes. 42 The values of substituent constants (p, E s , MR, B 1 , and B 5 ) have been taken from the literature [43][44][45][46][47][48] and the QSAR regression analyses were executed with the C-QSAR program. 49 Multivariate linear/nonlinear regression models were used.…”

Section: M a T E R I A L S A N D M E T H O D Smentioning

confidence: 99%

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Pontiki

Hadjipavlou‐Litina

2006

Medicinal Research Reviews

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This paper contains a quantitative structure activity relationship (QSAR) study for lipoxygenase (LO) inhibitors. It reveals that in almost all cases, the clog P parameter plays an important part in the QSARs (linear or bilinear model). In some cases the steric factors such as the overall molar refractivity (CMR) or the substituents molar refractivity (MR) (linear or parabola) are important. Electronic effects are comparatively unimportant. The study shows that log P as calculated from the Clog P program is suitable for this form of QSAR study.

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Section: M a T E R I A L S A N D M E T H O D Smentioning

confidence: 99%

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Pontiki

Hadjipavlou‐Litina

2006

Medicinal Research Reviews

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“…A satisfactory correlation of log P with a is achieved through the additional inclusion of the sum of the Taft E s values of the substituents R 1 and R 2 [29], which is presented by Eq. (3).…”

Section: Resultsmentioning

confidence: 99%

Solvent effects on the structure-property relationship of anticonvulsant hydantoin derivatives: A solvatochromic analysis

Trišović

Valentić

Ušćumlić

2011

Chemistry Central Journal

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Considering the pharmaceutical importance of hydantoins, a set of 25 derivatives of phenytoin, nirvanol and 5-methyl-5-phenylhydantoin, the lipophilicities of which were gradually increased by the introduction of different alkyl, cycloalkyl and alkenyl groups in position N3, was synthesized. Their properties under consideration were either estimated empirically, by UV/Vis spectroscopy, or calculated using established medicinal chemistry software. The UV absorption spectra of the investigated compounds were recorded in the region from 200 to 400 nm, in selected solvents of different polarities. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. Furthermore, the relationships between solvent-solute interactions and selected structural features of the solutes, which are believed to markedly affect the processes of absorption, distribution, metabolism, excretion and toxicity (ADMETox), were discussed. Satisfactory correlations were found between hydrogen bonding properties and solute size and the in silico calculated bioactivity descriptors, in particular %Abs. (human intestinal absorption), log BB (blood-brain barrier permeation) and log kA (protein binding affinities) parameters. In view of the results of this study, the investigated hydantoin derivatives met the pharmacokinetic criteria for pre-selection as drug candidates and qualified them for the pharmacodynamic phase of antiepileptic drug development.

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“…13 7 In eq. 9 [23] the E s term for substituents para to -NH 2 does not formulate better correlation. However, it seems that the para-substituents depress the inhibition of the antioxidant activity as brought out by E s .…”

Section: Ii) Phenyl-butenones Iv) Coumarinsmentioning

confidence: 89%

A Review on Quantitative Structure-Activity Relationships (QSARs) of Natural and Synthetic Antioxidants Compounds

Kontogiorgis

Pontiki²,

Hadjipavlou‐Litina³

2005

MRMC

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During the last decade an increasing number of reports describe the roles of active oxygen species in the development or exacerbation of various kinds of diseases. Antioxidants are of great interest because of their involvement in important biological and industrial processes. They have been found to possess anticancer, anti-cardiovascular, anti-inflammatory and many other activities. Many attempts have been made to elucidate the QSAR of antioxidants by using different physicochemical parameters. Unfortunately the limited number of antioxidants and the unavailable sigma Hammett values of complex substituents did not lead to significant results in regression analysis. The redox potentials are well correlated to the antioxidant activities. In this report we will attempt to collect and discuss all the published results concerning the QSAR research on natural and synthetic antioxidants compounds.

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Quantitative Models of Steric Effects

Cited by 174 publications

References 128 publications

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Solvent effects on the structure-property relationship of anticonvulsant hydantoin derivatives: A solvatochromic analysis

A Review on Quantitative Structure-Activity Relationships (QSARs) of Natural and Synthetic Antioxidants Compounds

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