Lipophilicity of Barbiturates Determined by TLC

Kępczyńska, Elżbieta; Bojarşki, Jacek; Pyka, Alina

doi:10.1081/jlc-120025523

Cited by 4 publications

(2 citation statements)

References 19 publications

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“…However, this 'shake-fl ask' method is still being used as a reference for some compounds (Pliška et al, 1996, p. 402). Other methods include reversed-phase 262 high-performance liquid chromatography (RP-HPLC; Musilek et al, 2008;Musiol et al, 2008;Sztanke et al, 2008), reversed-phase thin-layer chromatography (RP-TLC; Inglot et al, 2008;Kępczyńska et al, 2007;Malawska et al, 2008) and diff erent computational procedures (Bajda et al, 2008;Kępczyńska et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Achrem-Achremowicz

Kępczyńska

Zylewski

et al. 2009

Biomedical Chromatography

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A series of superlipophilic or highly lipophilic semisynthetic betulin derivatives was prepared and their relative lipophilicity was measured by reversed-phase thin-layer chromatography (RP-TLC) at different pH values using 1,4-dioxane-acetate buffer mixtures as mobile phases. Cholesterol, 17beta-estradiol and pure betulin were used as the reference compounds. Linear relationships were found between R(M) values and 1,4-dioxane concentrations in the mobile phases. LogP values were also calculated with computer programs ACD/LogP (ChemSketch 11.0, Advanced Chemistry Development Inc.) and ClogP (Daylight Chemical Information Systems Inc.). The empirical and theoretical data were compared, and the R(M0) values correlated well with logP. Two of the synthesized betulin derivatives are reported for the first time.

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Section: Introductionmentioning

confidence: 99%

Synthesis of betulin derivatives and the determination of their relative lipophilicities using reversed‐phase thin‐layer chromatography

Achrem-Achremowicz

Kępczyńska

Zylewski

et al. 2009

Biomedical Chromatography

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“…The lipophilicity of barbiturates is an important parameter which enhances anesthetic onset [ 27 ]. It can be improved by replacing oxygen by a sulfur [ 28 ], as seen with the very short acting barbiturate thiopenthal. Substituents on the carbons of the barbituric acid scaffold also have a great influence on the pharmacological activity [ 27 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

New Methodology for the Synthesis of Thiobarbiturates Mediated by Manganese(III) Acetate

Bouhlel¹,

Curti²,

Vanelle³

2012

Molecules

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A three step synthesis of various thiobarbiturate derivatives 17–24 was established. The first step is mediated by Mn(OAc)3, in order to generate a carbon-carbon bond between a terminal alkene and malonate. Derivatives 1–8 were obtained in moderate to good yields under mild conditions. This key step allows synthesis of a wide variety of lipophilic thiobarbiturates, which could be tested for their anticonvulsive or anesthesic potential.

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