STUDYING RETENTION BEHAVIOR, LIPOPHILICITY AND PHARMACOKINETIC CHARACTERISTICS OF N-SUBSTITUTED PHENYL-2-CHLOROACETAMIDES

The biological activity of compounds is mostly determined by its physical and structural characteristics. Among the many molecular descriptors that may indicate a potential biological activity of a compound, lipophilicity occupies the most important place. Since chloroacetamides show a variety of physiological activity, the task of this study was to investigate the potential biological activity of newly synthesized derivatives of selected N-substituted phenyl-2-chloroacetamides. Analysis was performed by thin layer chromatography on reversed phase (RP18 F254s TLC), and the mobile phase consisted of mixtures of water-acetic acid and water-dimethylformamide. By varying the volume fraction of organic modifier chromatographic retention constants, RM0, of the compounds were determined. Тhen RM0 were correlated with the software calculated partition coefficient, log P, as a standard measure of lipophilicity. Also, RM0 were correlated with selected pharmacokinetic parameters: intestinal absorption, HIA, the ability to bind to plasma proteins, PPB, and the distribution through the blood-brain barrier, BBB.

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A comparative study concerning chromatographic retention and computed partition coefficients of some precursors of peraza crown ethers

Open Chemistry ◽

10.2478/s11532-010-0095-y ◽

2010 ◽

Vol 8 (6) ◽

pp. 1203-1209 ◽

Cited By ~ 2

Author(s):

Cristina Onişor ◽

Gabriela Blăniţă ◽

Maria Coroş ◽

Monica Bucşa ◽

Mircea Vlassa ◽

...

Keyword(s):

Comparative Study ◽

Crown Ethers ◽

Partition Coefficients ◽

High Performance ◽

Correlation Coefficients ◽

Reversed Phase ◽

Neural Network Modeling ◽

Log P ◽

Chromatographic Retention ◽

P Values

AbstractRetention 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.

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RETENTION BEHAVIOR AND BIOLOGICAL ACTIVITY OF N-SUBSTITUTED-2-PHENYLACETAMIDE DERIVATES

Contemporary Materials ◽

10.7251/comen1401124v ◽

2014 ◽

Vol 5 (1) ◽

Author(s):

Đenđi Vaštag ◽

Suzana Apostolov ◽

Borko Matijević ◽

Jelena Nakomčić ◽

Aleksandar Marinković

Keyword(s):

Biological Activity ◽

Biological Activities ◽

Biological Properties ◽

Reversed Phase ◽

Chromatographic Retention ◽

Wide Range ◽

Structure Retention ◽

The Mathematical Model ◽

The Relationship ◽

Layer Chromatography

Phenylacetamide derivatives are a group of compounds that exhibit a wide range of biological activities as analgetic, anticonvulsant, pesticide, cytostatic. It is well known that the biological activity and the field of activity of the substance are greatly dependent on its physical, chemical and structural properties. In this paper, we applied QSRR analysis (Quantitative Structure Retention Relationships), which is based on the prediction of biological properties of compounds based on their chromatographic retention behaviors. To that end, retention constants of investigated N-substituted-2-phenylacetamide were determined by reversed phase thin-layer chromatography, (HPTLC RP18 F254s) in the presence of different volume fractions of n-propanol and tetrahydrofuran. The resulting data were correlated with molecular descriptors determined in different ways in order to establish the mathematical model that describes the relationship between retention properties and biological activities of investigated phenylacetamides.

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ChemInform Abstract: Syntheses of N,S-Substituted 4-Chloro-2-mercapto-5-methylbenzenesulfonamide Derivatives with Potential Biological Activity.

ChemInform ◽

10.1002/chin.200922083 ◽

2009 ◽

Vol 40 (22) ◽

Author(s):

E. Pomarnacka ◽

A. Kornicka ◽

P. J. Bednarski ◽

A. Charkiewicz

Keyword(s):

Biological Activity ◽

Potential Biological Activity

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Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Molecules ◽

10.3390/molecules26092511 ◽

2021 ◽

Vol 26 (9) ◽

pp. 2511

Author(s):

Petra R. Varga ◽

György Keglevich

Keyword(s):

Biological Activity ◽

Solvent Free ◽

Trialkyl Phosphite ◽

Catalyst Free ◽

Potential Biological Activity

The Kabachnik–Fields reaction, comprising the condensation of an amine, oxo compound and a P-reagent (generally a >P(O)H species or trialkyl phosphite), still attracts interest due to the challenging synthetic procedures and the potential biological activity of the resulting α-aminophosphonic derivatives. Following the success of the first part (Molecules 2012, 17, 12821), here we summarize the synthetic developments in this field accumulated in the last decade. The procedures compiled include catalytic accomplishments as well as catalyst-free and/or solvent-free “greener” protocols. The products embrace α-aminophosphonates, α-aminophosphinates, and α-aminophosphine oxides along with different bis derivatives from the double phospha-Mannich approach. The newer developments of the aza-Pudovik reactions are also included.

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Predicting Pharmacokinetic Properties of Potential Anticancer Agents via Their Chromatographic Behavior on Different Reversed Phase Materials

International Journal of Molecular Sciences ◽

10.3390/ijms22084257 ◽

2021 ◽

Vol 22 (8) ◽

pp. 4257

Author(s):

Małgorzata Janicka ◽

Anna Mycka ◽

Małgorzata Sztanke ◽

Krzysztof Sztanke

Keyword(s):

Liquid Chromatography ◽

Anticancer Agents ◽

Skin Permeation ◽

Reversed Phase ◽

Chromatographic Behavior ◽

Chromatographic Retention ◽

Quantitative Structure ◽

Animal Testing ◽

Structure Activity ◽

Pharmacokinetic Properties

The Quantitative Structure-Activity Relationship (QSAR) methodology was used to predict biological properties, i.e., the blood–brain distribution (log BB), fraction unbounded in the brain (fu,brain), water-skin permeation (log Kp), binding to human plasma proteins (log Ka,HSA), and intestinal permeability (Caco-2), for three classes of fused azaisocytosine-containing congeners that were considered and tested as promising drug candidates. The compounds were characterized by lipophilic, structural, and electronic descriptors, i.e., chromatographic retention, topological polar surface area, polarizability, and molecular weight. Different reversed-phase liquid chromatography techniques were used to determine the chromatographic lipophilicity of the compounds that were tested, i.e., micellar liquid chromatography (MLC) with the ODS-2 column and polyoxyethylene lauryl ether (Brij 35) as the effluent component, an immobilized artificial membrane (IAM) chromatography with phosphatidylcholine column (IAM.PC.DD2) and chromatography with end-capped octadecylsilyl (ODS) column using aqueous solutions of acetonitrile as the mobile phases. Using multiple linear regression, we derived the statistically significant quantitative structure-activity relationships. All these QSAR equations were validated and were found to be very good. The investigations highlight the significance and possibilities of liquid chromatographic techniques with three different reversed-phase materials and QSARs methods in predicting the pharmacokinetic properties of our important organic compounds and reducing unethical animal testing.

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Structural characteristics and biological activity of different alginate blocks extracted from brown seaweed Turbinaria ornata

Journal of Carbohydrate Chemistry ◽

10.1080/07328303.2021.1928155 ◽

2021 ◽

pp. 1-18

Author(s):

Thuy T. T. Thanh ◽

Thu T. M. Quach ◽

Van T. T. Tran ◽

Thanh V. Nguyen ◽

Shiho Suzuki ◽

...

Keyword(s):

Biological Activity ◽

Structural Characteristics ◽

Brown Seaweed ◽

Turbinaria Ornata

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SYNTHESIS OF NOVEL TRYPTOPHAN DERIVATIVES OF POTENTIAL BIOLOGICAL ACTIVITY

Journal of the Chilean Chemical Society ◽

10.4067/s0717-97072009000200018 ◽

2009 ◽

Vol 54 (2) ◽

Cited By ~ 3

Author(s):

RAFAT M MOHAREB ◽

NADIA A LOUCA ◽

GAMAL A ELMEGEED ◽

HANAA Y HANA

Keyword(s):

Biological Activity ◽

Potential Biological Activity ◽

Derivatives Of ◽

Tryptophan Derivatives

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Transport properties of concrete-like granular materials interacted by their microstructures and particle components

International Journal of Modern Physics B ◽

10.1142/s0217979218400118 ◽

2018 ◽

Vol 32 (18) ◽

pp. 1840011 ◽

Cited By ~ 27

Author(s):

Wenxiang Xu ◽

Hongguang Sun ◽

Wen Chen ◽

Huisu Chen

Keyword(s):

Transport Properties ◽

Granular Materials ◽

Soft Matter ◽

Volume Fraction ◽

Structural Characteristics ◽

Effective Diffusion ◽

Nonspherical Particles ◽

Structure Property ◽

Engineering Structures ◽

Component Structure

Granular materials as typical soft matter, their transport properties play significant roles in durability and service life in relevant practical engineering structures. Physico-mechanical properties of materials are generally dependent of their microstructures including interfacial and porous characteristics. The formation of such microstructures is directly related to particle components in granular materials. Understanding the interactive mechanism of particle components, microstructures, and transport properties is a problem of great interest in materials research community. The resulting rigorous component-structure-property relations are also valuable for material design and microstructure optimization. This review article describes state-of-the-art progresses on modeling particle components, interfacial and porous configurations and incorporating these internal structural characteristics into modeling transport properties of granular materials. We mainly focus on three issues involving the simulation for geometrical components, the quantitative characterization for interfacial and porous microstructures, and the modeling strategies for diffusive behaviors of granular materials. In the first aspect, in-depth reviews are presented to realize complex morphologies of geometrical particles, to detect the overlap between adjacent nonspherical particles, and to simulate the random packings of nonspherical particles. In the second aspect, we emphasize the development progresses on the interfacial thickness and porosity distribution, the interfacial volume fraction, and the continuum percolation of soft particles representing compliant interfaces and discrete pores. In the final aspect, a literature review is also provided on modeling of transport properties on the forefront of the effective diffusion and anomalous diffusion in multiphase granular materials. Finally, some conclusions and perspectives for future studies are provided.

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