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The study of the lipophilicity of some aminoalkanol derivatives with anticonvulsant activity
Author(s) -
Waszkielewicz Anna,
Szkaradek Natalia,
Pękala Elżbieta,
Galzarano Fabiola,
Marona Henryk
Publication year - 2010
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.1453
Subject(s) - lipophilicity , chemistry , anticonvulsant , partition coefficient , carbamazepine , chromatography , phenytoin , thin layer chromatography , acetone , stereochemistry , organic chemistry , psychology , epilepsy , neuroscience
Abstract A series of new (phenoxyethyl)aminoalkanol derivatives were synthesized and evaluated for their anticonvulsant activity. The most promising compound seemed to be ( R , S )‐1N‐[(2,6‐dimethyl)phenoxyethyl]amino‐2‐butanol, which displayed anti‐MES activity (in mice, i.p.) with protective index (TD 50 /ED 50 ) of 5.712, corresponding to that of phenytoin (6.6), carbamazepine (4.9) and valproate (1.7). The lipophilicity of compounds 1–17 exhibiting anticonvulsant activity was investigated. Their lipophilicities ( R M0 ) were determined using reversed‐phase thin‐layer chromatography (RP‐TLC) with a mixture of acetone and water as mobile phases. The partition coefficients of 1–17 (log P ) were also calculated using two computer programs (Pallas and ALOGPS) and compared with R M0 . The relationship between anticonvulsant activity and lipophilicity of the tested substances was estimated. Copyright © 2010 John Wiley & Sons, Ltd.