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Estimation of the lipophilicity of antiarrhythmic and antihypertensive active 1‐substituted pyrrolidin‐2‐one and pyrrolidine derivatives
Author(s) -
Kulig Katarzyna,
Malawska Barbara
Publication year - 2003
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.246
Subject(s) - lipophilicity , chemistry , partition coefficient , chromatography , high performance liquid chromatography , pyrrolidine , acetonitrile , reversed phase chromatography , stereochemistry
The lipophilicity of some antiarrhythmic and antihypertensive active 1‐[2‐hydroxy‐ or 1‐[2‐acetoxy‐3‐(4‐aryl‐1‐piperazinyl)propyl]pyrrolidin‐2‐one derivatives ( 1 – 12 ) has been investigated. Their lipophilicity ( R MO and log k ′) was determined by reversed‐phase thin‐layer chromatography and reversed‐phase high‐performance liquid chromatography with mixtures of acetonitrile and Tris buffer as mobile phases. The partition coefficients of compounds 1 – 12 (log P ScilogP ) were also calculated with the ScilogP program. Comparison of R MO , log k ′ and calculated log D 7.0 ScilogP values enabled calculation of clog D 7.0 TLC and clog D 7.0 HPLC values. Preliminary quantitative structure–activity relationship studies indicated that for active compounds there is a dependence between affinity for α 2 ‐adrenoceptors and their clog D 7.0 HPLC values. Copyright © 2003 John Wiley & Sons, Ltd.