Estimation of the lipophilicity of antiarrhythmic and antihypertensive active 1-substituted pyrrolidin-2-one and pyrrolidine derivatives.
ABSTRACT 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 alpha(2)-adrenoceptors and their clog D(7.0 HPLC) values.
- Jpc-journal of Planar Chromatography-modern Tlc - JPC-J PLANAR CHROMAT-MOD TLC. 01/2009; 22(4):255-263.
- Jpc-journal of Planar Chromatography-modern Tlc - JPC-J PLANAR CHROMAT-MOD TLC. 01/2009; 22(2):141-144.
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ABSTRACT: The lipophilicity of anticancer and immunosuppressant active 1,8-diazaphenothiazine derivatives (1: -16: ) has been investigated. Their lipophilicity (RM0 and log PTLC) was determined by reversed-phase thin-layer chromatography with mixtures of acetone and TRIS buffer as mobile phases. The parameter RM0 and specific hydrophobic surface area b were significantly intercorrelated showing congeneric classes of dipyridothiazines. The parameter RM0 was discussed in the terms of the structure-lipophilicity relationships and transformed into parameter log PTLC by use of the calibration curve. The lipophilicity was correlated with molecular and biomolecular descriptors (human intestinal absorption, blood-brain barrier, plasma protein binding, MDCK) and in vitro tumor necrosis factor alpha inhibition and antiproliferative activity.Journal of chromatographic science 06/2014; · 0.79 Impact Factor