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1
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Determination of lipophilicity for antitumor acridinone derivatives supported by gradient high-performance liquid chromatography method

100%
Koba M., Belka M., Ciesielski T., Bączek T.
Open Chemistry
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2012
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vol. 10
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issue 1
216-223
EN
The lipophilicity values of selected acridinone (imidazoacridinone and triazoloacridinone) derivatives were measured by gradient reversed-phase high-performance liquid chromatography (RP-HPLC) using a C18 stationary phase with a water/acetonitrile mixture as a mobile phase. The retention times obtained served as input data and appropriate log kw values (i.e., the retention factor log kw extrapolated to 0% organic modifier) as an alternative to log P were calculated using the DryLab program. The relationships between the lipophilicity (log kw) and the chemical structure of the studied compounds, as well as correlation between experimentally determined lipophilicities (log kw) and log P data calculated using some commonly available software, are discussed.
2
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Study of lipophilicity of alpha-asarone derivatives and their deterrent activity against the Colorado potato beetle

80%
Łozowicka B., Kaczyński P., Nawrot J.
Open Chemistry
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2013
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vol. 11
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issue 12
2120-2133
EN
Five positional isomers and thirty derivatives of alpha-asarone wereobtained as a bioactive set of substances, and their deterrent activity against the Colorado potato beetle was studied. The lipophilicity values of thirty-six compounds were determined by using experimental, chromatographic and theoretical methods. The logk w values for all compounds were determined by reversed-phase high-performance liquid chromatography using five different columns. The octan-1-ol/water partition coefficients values were determined experimentally as a measure of lipophilicity. For the purpose of comparison, theoretical lipophilic parameters for all compounds were calculated with the use of chemical programs. The experimental, chromatographic and calculated values were compared using linear regression analysis. The most significant correlations were found between the chromatographic lipophilicities using methanol/water for all tested columns and calculated values. It has been found that 13 compounds have the lowest lipophilicities, which correspond to deterrent activity. The presented results show that the computational method is useful for determining the lipophilicity of a series of homologues, but not for positional isomers. In addition, this study shows that determination of lipophilicity using HPLC with various stationary phases is practical and reasonable for all alpha-asarone derivatives. [...]
3
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A comparative study concerning chromatographic retention and computed partition coefficients of some precursors of peraza crown ethers

80%
Onişor C., Blăniţă G., Coroş M., Bucşa M., Vlassa M., Sârbu C.
Open Chemistry
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2010
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vol. 8
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issue 6
1203-1209
EN
Retention indices for some precursors of peraza crown ethers were determined by reversed phase high-performance thin layer chromatography on RP-18 plates with methanol-water in different volume proportions as mobile phase. The Log P values for the same compounds were calculated using different computer programs: SciQSAR, SciLogP, Chem3D Ultra 8.0, XLOGP (based on atom contributions), Chemaxon and KOWWIN (based on atom/fragment contributions), cLogP (based on fragmental contributions), ALOGPS and IAlogP (based on atom-type electrotopological-state indices and neural network modeling). A comparative study concerning lipophilic parameters (RM0, b and ϕ0) and computed partition coefficients has been developed. Taking into account the correlation coefficients between determined and calculated Log P values, it seems that RM0 and b are less suitable than ϕ0 for estimating lipophilicity of the compounds investigated, and cLogP and ALOGPS provide the best correlations with experimental values.
4
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RP-HPLC determination of lipophilicity in series of quinoline derivatives

80%
Musiol R., Jampilek J., Podeszwa B., Finster J., Tabak D., Dohnal J., Polanski J.
Open Chemistry
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2009
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vol. 7
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issue 3
586-597
EN
In the present paper we describe results on the synthesis and lipophilicity determination of a series of biologically active compounds based on their heterocyclic structure. For synthesis of styrylquinoline-based compounds we applied microwave irradiation and solid phase techniques. The correlation between RP-HPLC retention parameter log k (the logarithm of retention factor k) and log P data calculated in various ways is discussed, as well as, the relationships between the lipophilicity and the chemical structure of the studied compounds. [...]
5
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A TLC Study of the lipophilicity of thirty-two acetylcholinesterase inhibitors - 1,2,3,4-tetrahydroacridine and 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives

70%
Szymański P., Skibiński R., Liszka M., Jargieło I., Mikiciuk-Olasik E., Komsta Ł.
Open Chemistry
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2013
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vol. 11
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issue 6
927-934
EN
The lipophilicity of thirty-two novel acetylcholinesterase (AChE) inhibitors - 1,2,3,4-tetrahydroacridine and 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives was studied by thin layer chromatography. The analyzed compounds were chromatographed on RP-18, RP-8, RP-2, CN and NH2 stationary phases with dioxane - citric buffer pH 3.0 binary mobile phases containing different proportions of dioxane. RM values for pure water were extrapolated from the linear Soczewiński-Wachtmeister equation and six compounds with known literature log P values were used as reference calibration data set for computation of experimental log P values. [...] The obtained results were compared with computationally calculated partition coefficients values (AlogPs, AClogP, AlogP, MlogP, KOWWIN, XlogP2, XlogP3) by PCA and significant differences between them were observed.
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