A study of the lipophilicity of amide derivatives of<i>α</i>-(1,2,3,4-tetrahydroisoquinolin-2-yl)-<i>γ</i>-hydroxybutyric acid by use of RP-TLC and calculation

Więckowski, Krzysztof; Czaja, Anna; Woźniak, Anna; Musiał, Anna; Malawska, Barbara

doi:10.1556/jpc.20.2007.2.6

Cited by 11 publications

(5 citation statements)

References 20 publications

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“…The isocratic capacity factors (obtained at a single selected and hydrogen bonding interactions, whereas the classical reversed-phase chromatography provides the retention of analytes solely on the basis of hydrophobicity (Barbato et al, 2005;Lepont and Poole, 2002;Li et al, 2007;Ong et al, 1996;Pidgeon et al, 1995). This work is a part of our physicochemical and pharmacological studies in a group of anticonvulsant active compounds, derivatives of γ-aminobutyric acid (GABA), which is an important inhibitory neurotransmitter in the central nervous system (Malawska et al, 2003(Malawska et al, , 2004Wi^ckowski et al, 2007). The aim of this study was to determine and compare the lipophilicity of a series of α-(4-phenylpiperazin-1-yl)-γ-phthalimidobutyramides measured using reversed-phase chromatography (TLC and HPLC) and immobilized artificial membrane chromatography (IAM-HPLC) and calculated using commercially available programs such as Pallas and CaChe.…”

Section: Rp-hlpcmentioning

confidence: 99%

The study of the lipophilicity of α‐(4‐phenylpiperazin‐1‐yl)‐γ‐phthalimidobutyramides using chromatographic and computational methods

Malawska¹,

Kulig²,

Bucki³

et al. 2008

Biomedical Chromatography

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The lipophilicity of the series of alpha-(4-phenylpiperazin-1-yl)-gamma-phthalimido-butyramides (1-8) has been investigated. Several methods, like reversed-phase thin-layer chromatography and high-performance liquid chromatography using reversed-phase RP18 and IAM.DD2 columns, were applied to determine RMO, log k0 and log k(0IAM) factors. The RP-TLC investigations were performed in mixtures of acetone-water and acetonitrile-water. For RP-HPLC method mixtures of acetonitrile, water and 0.01% TFA were used as the mobile phases while for IAM.DD2 investigations mixtures of acetonitrile and water were applied. The partition coefficients of compounds (1-8) were also calculated with the Pallas and CAChe programs. All the obtained data, both from experimental methods and computational calculations, were compared and a suitable conclusion was reached.

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Section: Rp-hlpcmentioning

confidence: 99%

The study of the lipophilicity of α‐(4‐phenylpiperazin‐1‐yl)‐γ‐phthalimidobutyramides using chromatographic and computational methods

Malawska¹,

Kulig²,

Bucki³

et al. 2008

Biomedical Chromatography

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“…For example, their bioconcentration factors may be higher than those of parent methylsiloxanes because −Cl had larger lipophilicity than −CH 3 . 25 In the present study, the chlorination of cVMS − including octamethylcyclotetrasiloxane (D4), decamethylcyclopentasiloxane (D5), and dodecamethylcyclohexasiloxane (D6) − in the bleaching process of one papermaking factory, where PDMS and Cl 2 were both used, was investigated together with the removal of the chlorinated cVMS in the coupled wastewater treatment processes. The objectives of this study were 2-fold: (1) to test the hypothesis that cVMS could be chlorinated in the papermaking processes under this special circumstance and (2) to compare the fate and occurrence of the chlorinated cVMS with those of nonchlorinated cVMS analogs in papermaking wastewater treatment processes.…”

Section: Introductionmentioning

confidence: 99%

“…Although relevant studies were scarce, ecological effects of chlorinated methylsiloxanes may be different from those of their parent methylsiloxanes. For example, their bioconcentration factors may be higher than those of parent methylsiloxanes because −Cl had larger lipophilicity than −CH 3 …”

Section: Introductionmentioning

confidence: 99%

Chlorinated Methylsiloxanes Generated in the Papermaking Process and Their Fate in Wastewater Treatment Processes

Zhi

et al. 2016

Environ. Sci. Technol.

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Simulated experiments indicated that chlorinated volatile methylsiloxanes, detected by Q-TOF GC/MS, could be generated in a pulp-bleaching process, where poly(dimethylsiloxane)s fluids with volatile methylsiloxanes as impurities and molecular chlorine were used as a defoamer and bleaching agent, respectively. In the producing processes of one papermaking factory, the mean total concentrations of monochlorinated D4, D5, and D6, i.e., D3D(CHCl), D4D(CHCl), and D5D(CHCl), were 0.0430-287 μg/L in aqueous samples, while they were 0.0329-270 μg/g in solid samples. In the coupled papermaking-wastewater treatment processes, D3D(CHCl), D4D(CHCl), and D5D(CHCl) were detected in all water (0.113-8.68 μg/L) and solid samples (0.888-26.2 μg/g), with solid-water partition values (468-3982 L/kg) 1.08-4.82 times higher than those of their corresponding nonchlorinated analogs. The removing efficiencies of D3D(CHCl)-D5D(CHCl) in the whole wastewater treatment processes were 77.1-81.6%, and sorption to sludge (35.7-74.1%) and removal in the primary clarifier (7.19-32.5%) had major contributions to their total removal. Elimination experiments showed that 1) hydrolysis half-lives of D3D(CHCl)-D5D(CHCl) (0.9-346 h) in the primary clarifier (pH = 7.8-9.2) were 2.16-3.60 times shorter than those of their nonchlorinated analogs; 2) D3D(CHCl)-D5D(CHCl) were hardly degraded in oxic sludge treatment process, and their volatilization half-lives (7.38-21.1 h) in oxic sludge were 1.21-1.50 times longer than those of their nonchlorinated analogs.

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“…There are several reports dealing with preliminary studies on the biological activity of newly synthesized compounds from different chemical groups by use of RP-TLC methods [26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography

Hawrył¹,

Kuśmierz²,

Pisarczyk³

et al. 2012

Acta Chromatographica

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Summary. In this study, the chromatographic behavior of a newly synthesized series of 1,4-disubstituted thiosemicarbazide derivatives and products of their dehydrocyclization is presented. These compounds have been subjected to this study because they exhibit antimicrobial activity. The compounds have been chromatographed on RP-18 and on cyano-bonded silica chromatographic phases with eluents containing water and an organic modifier (methanol, dioxane, acetone, acetonitrile or tetrahydrofuran) of various concentrations. Statistically proved linear relationships between the retention parameter (R M ) and the concentration of organic modifier in the mobile phase allow the extrapolation procedure to obtain R ) were compared with the log P values calculated by use of four different software packages. The values of the correlation coefficients of these relationships are higher for the cyanopropyl phase than for RP-18. Moreover, in this work the influences of different mobile phase modifiers and adsorbent layers on experimentally obtained lipophilicity parameters were analyzed and compared. Generally, the best correlations were obtained for systems with the cyanopropyl-bonded stationary phase in comparison with RP-18.

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A study of the lipophilicity of amide derivatives ofα-(1,2,3,4-tetrahydroisoquinolin-2-yl)-γ-hydroxybutyric acid by use of RP-TLC and calculation

Cited by 11 publications

References 20 publications

The study of the lipophilicity of α‐(4‐phenylpiperazin‐1‐yl)‐γ‐phthalimidobutyramides using chromatographic and computational methods

The study of the lipophilicity of α‐(4‐phenylpiperazin‐1‐yl)‐γ‐phthalimidobutyramides using chromatographic and computational methods

Chlorinated Methylsiloxanes Generated in the Papermaking Process and Their Fate in Wastewater Treatment Processes

Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography

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