Theoretical scales of hydrogen bond acidity and basicity for application in QSAR/QSPR studies and drug design. Partitioning of aliphatic compounds.
J Chem Inf Comput Sci
; 44(3): 1042-55, 2004.
Article
em En
| MEDLINE
| ID: mdl-15154773
ABSTRACT
Phenomenological analysis of existing hydrogen bond (HB) donor and acceptor scales and apparent physical considerations have enabled the establishment of new quantitative scales of hydrogen bond basicity and acidity. Chemical structures represented by molecular graphs and the orbital electronegativities of Hinze and Jaffe are utilized as an input data. The scales obtained correlate well with several experimental solvent polarity scales such as and, pK(HB), and E(T)(30). To demonstrate the applicability of the new quantities, we have applied them to seven equilibrium partitioning data sets octanol-water, hexadecane-water, chloroform-water, gas-water, gas-octanol, gas-hexadecane, and gas-chloroform partition coefficients. The hydrogen bond descriptors when supplemented by a cavity-forming term and a dipolarity term show high performance in correlations of the partition coefficients of aliphatic compounds. These new HB descriptors can be used in studying hydrogen bonding and fluid phase equilibria as well as scoring functions in ligand docking and descriptors in ADME evaluations.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Desenho de Fármacos
Tipo de estudo:
Prognostic_studies
/
Qualitative_research
Idioma:
En
Revista:
J Chem Inf Comput Sci
Ano de publicação:
2004
Tipo de documento:
Article