dc.creatorMALVEZZI, Alberto
dc.creatorAMARAL, Antonia T. do
dc.date.accessioned2012-10-20T05:24:43Z
dc.date.accessioned2018-07-04T15:50:16Z
dc.date.available2012-10-20T05:24:43Z
dc.date.available2018-07-04T15:50:16Z
dc.date.created2012-10-20T05:24:43Z
dc.date.issued2010
dc.identifierEUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, v.41, n.5, p.631-635, 2010
dc.identifier0928-0987
dc.identifierhttp://producao.usp.br/handle/BDPI/31435
dc.identifier10.1016/j.ejps.2010.09.003
dc.identifierhttp://dx.doi.org/10.1016/j.ejps.2010.09.003
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1628073
dc.description.abstractIn this work, a series of 10 structural procaine analogs have been synthesized in order to investigate the structural features affecting the stability of ion pair formation and its influence on the lipophilicity of ionizable compounds. The structural variation within this series was focused on the terminal nitrogen substituents and on the intermediate chain linkage nature. The hydrophobic parameters log P(n) and log P(i) (partition coefficient of the neutral and ionic species, respectively), as well as the ionization constants pK(a) and pK(a)(oct), were obtained from log D-pH profiles measured at pH values ranging from 2 to 12. The difference between log P(i) and log P(n) values (i.e. difflog P) of each prepared compound was considered a measure of the stability of ion pair formation. In this set, the difflog P values varied nearly over one log unit, ranging from -2.40 to -3.37. It has been observed that the presence of hydrogen bonding groups (especially donor) and low steric hindrance around the terminal amine ionizable group increases the relative lipophilicity of the ionic species as compared to the corresponding neutral species. These results were interpreted as due to the increased stability of ion pairs of the compounds bearing these structural features. (C) 2010 Elsevier B.V. All rights reserved.
dc.languageeng
dc.publisherELSEVIER SCIENCE BV
dc.relationEuropean Journal of Pharmaceutical Sciences
dc.rightsCopyright ELSEVIER SCIENCE BV
dc.rightsrestrictedAccess
dc.subjectPartition coefficient
dc.subjectIon pair
dc.subjectProcaine analogs
dc.subjectLipophilicity
dc.subjectlogD-pH profile
dc.subjectShake-flask
dc.titleIon pair stabilization effects on a series of procaine structural analogs
dc.typeArtículos de revistas


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