Hydrogen-bonding parameter and its significance in quantitative structure-activity studies

Journal of Medicinal Chemistry
1977.0

Abstract

When the relative hydrogen-bonding effect of drugs on phases involved in the binding at the site of biological action differs from that in the 1-octanol-H2O partitioning phases used as the reference to estimate the hydrophobicity, a parameter (or parameters) which represents the "extra" hydrogen-bonding effect on the biological activity is required in the Hansch-type correlations. As a first approximation, the effect is analyzed in terms of the ratio of hydrogen-bonding association constants and the ratio of molarities of hydrogen-bonding species constituting the biological and organic phases. Sometimes, the association constants in both phases are so similar that they are not important in determining the extra hydrogen-bonding effect. The net result is that the effect is expressible by an indicator variable term the slope of which corresponds to the molarity ratio. The variable only applies to substituents having appreciable association capability in correlating a certain biological action exhibited by a series of congeners.

Knowledge Graph

Similar Paper

Hydrogen-bonding parameter and its significance in quantitative structure-activity studies
Journal of Medicinal Chemistry 1977.0
Energy aspects of oil/water partition leading to the novel hydrophobic parameters for the analysis of quantitative structure-activity relationships
Journal of Medicinal Chemistry 1992.0
A quantitative structure-activity relationship and molecular graphics analysis of hydrophobic effects in the interactions of inhibitors with alcohol dehydrogenase
Journal of Medicinal Chemistry 1986.0
Molecular connectivity. 6. Examination of the parabolic relationship between molecular connectivity and biological activity
Journal of Medicinal Chemistry 1976.0
Quantitative structure-activity relationships. 2. A mixed approach, based on Hansch and Free-Wilson analysis
Journal of Medicinal Chemistry 1976.0
QSAR study on adenosine kinase inhibition of pyrrolo[2,3- d ]pyrimidine nucleoside analogues using the hansch approach
Bioorganic & Medicinal Chemistry Letters 2002.0
Use of distribution coefficients in quantitative structure-activity relations
Journal of Medicinal Chemistry 1977.0
Quantitative structure-activity relations for 5-substituted 8-hydroxyquinolines as inhibitors of dental plaque
Journal of Medicinal Chemistry 1977.0
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogs
Journal of Medicinal Chemistry 1979.0
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters
Journal of Medicinal Chemistry 1990.0