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Theoretical scales of hydrogen bond acidity and basicity for application in QSAR/QSPR studies and drug design. Partitioning of aliphatic compoundsстатья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
- Авторы: Oliferenko A.A., Oliferenko P.V., Huddleston J.G., Rogers R.D., Palyulin V.A., Zefirov N.S., Katritzky A.R.
- Журнал: Journal of Chemical Information and Modeling
- Том: 44
- Номер: 3
- Год издания: 2004
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 1042
- Последняя страница: 1055
- DOI: 10.1021/ci0342932
- Аннотация: 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 Sigmabeta(2)(H) and Sigmaalpha(2)(H), pK(HB), and E-T(30). To demonstrate the applicability of the new 2 2 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.
- Добавил в систему: Зефиров Николай Серафимович