Study of the Lipophilicity and Retention Behavior of Some s-Triazine Derivatives on Aminoplast and Cellulose

JPC – Journal of Planar Chromatography – Modern TLC - The chromatographic behavior of four groups of s-triazine derivatives (15 compounds) has been studied on aminoplast and cellulose...     

Study of Quantitative Structure-Retention Relationships for s-Triazine Derivatives in Different RP HPTLC Systems

JPC – Journal of Planar Chromatography – Modern TLC - Quantitative structure-retention relationships (QSRR) have been used to study the chromatographic behavior of some s-triazines....     

RP TLC Determination of the Lipophilicity of Anticancer-Active Propargyl Thioquinolines

JPC – Journal of Planar Chromatography – Modern TLC - The lipophilicity of fifteen anticancer-active propargyl thioquinolines has been determined by reversed-phase thin-layer...     

Chromatographic Evaluation of the Lipophilicity of N-Phenyltrichloroacetamide Derivatives using Micellar TLC and OPLC

JPC – Journal of Planar Chromatography – Modern TLC - Micellar liquid chromatography (MLC) has been used to study the lipophilicity of eight newly synthesized N-phenyltrichloroacetamide...     

A TLC Study of the Lipophilicity of New Antimycobacterial Active Benzoxazine Derivatives Containing a Thioxo Group

JPC – Journal of Planar Chromatography – Modern TLC - Experimental RM values of a series of 3-(4-alkylphenyl)-4-thioxo-2 H-1,3-benzoxazine-2(3H)-ones and...     

Antioxidant and Antitumor Activities of Newly Synthesized Hesperetin Derivatives

Hesperetin is a class of natural products with a wide range of sources and remarkable biological activities. In this study, we described the synthesis of a series of novel hesperetin derivatives and evaluated the in vitro antioxidant and antitumor activity of these compounds. Eleven novel compounds were synthesized in moderate yields. The compounds synthesized in this work exhibited antioxidant activities against DPPH and ABTS free radicals in a dose-dependent manner. Among them, compound 3f had the best antioxidant activity, with IC₅₀ of 1.2 μM and 24 μM for DPPH and ABTS, respectively. The antitumor activity of the compounds against human cancer cell lines, such as breast MCF-7, liver HepG2, and cervical Hela, was determined by a standard 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay. Three compounds had moderate IC₅₀ values. Interestingly, compound 3f had better biological activity than hesperetin, which matches the prediction by Maestro from Schrödinger. Therefore, the new hesperidin derivative is a promising drug for the treatment of cancer due to its effective antitumor activity. The results also suggested that the antitumor activities of hesperetin derivatives may be related to their antioxidant activities.     

Synthesis and Antiproliferative Activity of Some Newly Synthesized Pyrazolopyridine Derivatives

Russian Journal of General Chemistry - A series of pyrazolopyridine derivatives is synthesized from emyl-4-amino-6-memyl-1-(mphtha[1,2-d]-[1,3]tmazol-2-yl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate...     

Synthesis and Antimicrobial Evaluation of Newly Synthesized N,S‐Bisphosphonate Derivatives

An easy strategy for the synthesis of tetraethyl‐2‐(3‐mercapto‐4H‐1,2,4‐triazol‐4‐ylamino)‐2‐(aryl)ethane‐1,1‐diyldiphosphonate and tetraethyl‐(6‐(aryl)‐5,6‐dihydro[1,2,4]triazolo[3,4‐b]‐[1,3,4]thiadiazol‐6‐yl)methylenediphosphonate derivatives with reasonable 67–85% overall yields has been developed. The approach was achieved via applying Wadsworth–Horner–Emmons reagent, tetraethylmethylenebisphosphonate, to 4‐(arylideneamino)‐4H‐1,2,4‐triazole‐3‐thiols under phase‐transfer catalysis conditions. Screening results of antimicrobial potency for 12 out of 17 methylene‐1,1‐bisphosphonate products were reported. Two of the tested thiadiazolomethylenebisphosphonates displayed better spectrum of antimicrobial activity against the pathogens, compared with that of the positive controls.     

Lipophilicity Behavior of Model and Medicinal Compounds containing a suilfide,sulfoxide, or sulfone moiety

This study was designed to unravel lipophilicity changes associated with the oxidation state of the S-atom in model compounds, drugs, and metabolites, special attention being given both to intermolecular and intramolecular effects. The methods used were experimental (potentiometry, CPC, and shake-flask techniques to measure lipophilicity, ¹³C-NMR spectroscopy to investigate tautomeric equilibria) and computational (quenched molecular dynamics and molecular lipophilicity potential). Simple, monofunctional model compounds were used to assess intermolecular forces, as revealed by the Δlog P_oct–alk and Δlog P_oct–chf parameters. Drugs and their metabolites proved to be good probes to study intramolecular effects in both neutral and anionic forms, as revealed by the difference between calculated and experimental log P_oct values (the diff(log P^exp–calc) parameter). Sulindac and its metabolites showed a normal partitioning behavior, whereas the lipophilicity of sulfmpyrazone and its metabolites' was markedly affected by tautomeric and conformational equilibria.     

Synthesis and Antitumor Evaluation of Some Newly Synthesized Pyrazolopyrimidine and Pyrazolotriazolopyrimidine Derivatives

A series of novel pyrazolo[3,4-d]pyrimidine 2b, 3, 5b, pyrazolotetrazolopyrimidine 4, and pyrazolotriazolopyrimidine derivatives 6a,b–10a,b have been synthesized and characterized by elemental analysis and spectroscopic data. Furthermore, the cytotoxicity and in vivo antitumor evaluation of some prepared compounds have been assessed, and derivatives 1a and 6b revealed promising activity in comparison to that of Cisplatin.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis,Antibacterial Activity,and Cytotoxicity of Newly Synthesized N-Substituted 5,6-Dimethoxy-1H-indole Derivatives

Russian Journal of General Chemistry - A series of novel functionalized N-substituted 5, 6-dimethoxy-1H-indole derivatives is synthesized. All products are evaluated for antibacterial activity...     

Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5-Disubstituted Furane Derivatives

Newly designed and synthesized cyano, amidino and acrylonitrile 2,5-disubstituted furane derivatives with either benzimidazole/benzothiazole nuclei have been evaluated for antitumor and antimicrobial activity. For potential antitumor activity, the compounds were tested in 2D and 3D cell culture methods on three human lung cancer cell lines, A549, HCC827 and NCI-H358, with MTS cytotoxicity and BrdU proliferation assays in vitro. Compounds 5, 6, 8, 9 and 15 have been proven to be compounds with potential antitumor activity with high potential to stop the proliferation of cells. In general, benzothiazole derivatives were more active in comparison to benzimidazole derivatives. Antimicrobial activity was evaluated with Broth microdilution testing (according to CLSI (Clinical Laboratory Standards Institute) guidelines) on Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus. Additionally, Saccharomyces cerevisiae was included in testing as a eukaryotic model organism. Compounds 5, 6, 8, 9 and 15 showed the most promising antibacterial activity. In general, the compounds showed antitumor activity, higher in 2D assays in comparison with 3D assays, on all three cell lines in both assays. In natural conditions, compounds with such an activity profile (less toxic but still effective against tumor growth) could be promising new antitumor drugs. Some of the tested compounds showed antimicrobial activity. In contrast to ctDNA, the presence of nitro group or chlorine in selected furane-benzothiazole structures did not influence the binding mode with AT-DNA. All compounds dominantly bound inside the minor groove of AT-DNA either in form of monomers or dimer and higher-order aggregates.     

The Retention Behavior of Some Atypical Antipsychotic Drugs in Normal-Phase TLC

JPC – Journal of Planar Chromatography – Modern TLC - Chromatographic behavior in normal-phase thin-layer chromatog-raphy has been investigated for six atypical antipsychotic drugs...     

TLC Retention Behavior of Brodifacoum,Bromadiolone, and Coumatetralyl and their Impurities on Different Adsorbents

JPC – Journal of Planar Chromatography – Modern TLC - The chromatographic behavior of three biocidal technical materials, rodenticide active ingredients brodifacoum, bromadiolone, and...     

Study of RP HPLC Retention Behaviours in Analysis of Carotenoids

For determination of selected carotenoids, various types of columns for high-performance liquid chromatography (HPLC) with different properties have been used. The characteristics of the laboratory-used packing material containing monomeric alkyl-bonded phases (C₁₈, C₃₀) and phenyl as well as phenyl-hexyl stationary phases were studied. The retention data of the examined compounds were used to determine the hydrophobicity and silanol activity of stationary phases applied in the study. The presence of the polar and carboxyl groups in the structure of the bonded ligand strongly influences the polarity of the stationary phase. Columns were compared according to methylene selectivity using a series of benzene homologues. The measurements were done using a methanol–water mobile phase. Knowledge of the properties of the applied stationary phase provided the possibility to predict the RP HPLC retention behaviours in analysis of carotenoids including lutein, lycopene and β-carotene. The composition of the mobile phase, the addition of triethylamine and the type of stationary phase had been taken into account in designing the method of carotenoid identification. Also a monolithic column characterised by low hydrodynamic resistance, high porosity and high permeability was applied. The presented results show that the coverage density of the bonded ligands on silica gel packings and length of the linkage strongly influence the carotenoid retention behaviours. In our study, the highest retention parameters for lutein, lycopene and β-carotene were observed for C₃₀ and C₁₈ stationary phase. This effect corresponds with pore size of column packing greater than 100 Å and carbon content higher than 11 %.     

反相高效液相色谱对8种噻唑类衍生物保留性能的研究

在ＯＤＳ反相柱上，考察了不同浓度下的甲醇／水对８种噻唑衍生物保留值的影响。并把不同浓度的冲洗剂所得保留值和关系式ｌｎＫ′＝ａ＋ｃＣｂ中的参数ａ、ｃ作线性关联，得到很好的相关性，同时考察了不同种类的无机盐和有机胺对噻唑类衍生物容量因子ｋ′的影响。     

Retention Behavior of Nucleic Acid Bases and Purine Derivatives on Titania

The retention of nucleic acid bases and purine derivatives on titania was studied using a 0.4 mM acetic acid–sodium acetate buffer (pH 6.0) and 70% aqueous methanol as mobile phases. We observed that the retention strength of tested analytes on titania was dependent on the structural differences between pyrimidine and purine skeletons and the variety and number of substituents. The retention order was purine derivatives with methyl groups, pyrimidine bases and purine derivatives with hydrophilic functional groups, which were retained most strongly on titania. We concluded that the retention of each analyte was caused by the analyte’s hydrophobicity in the case of purine derivatives with methyl groups and pyrimidine bases. In the case of purine and its derivatives with hydrophilic functional groups, it was considered that the retention was dependent on the analyte’s ability to form chelates, and the variety and number of functional groups on C6 and C2.     

Retention Data for Some Carbonyl Derivatives of Imidazo[2,1-c][1,2,4]triazine in Reversed-Phase Systems in TLC and HPLC and their Use for Determination of Lipophilicity. Part 1. Lipophilicity of 8-Aryl-3-phenyl-6,7-dihydro-4H-imidazo[2,1-c][1,2,4]triazin-4-ones

JPC – Journal of Planar Chromatography – Modern TLC - Thirteen carbonyl derivatives of imidazo [2,1-c][1,2,4]triazine have been synthesized as a new bioactive set of substances....     

Study of Lipophilicity and Application of Selected Structural Descriptors in QSAR Analysis of Nicotinic Acid Derivatives. Investigations on RP18WF254 Plates. Part II

JPC – Journal of Planar Chromatography – Modern TLC - Nicotinic acid (NAC) and its derivatives methyl nicotinate (MN), ethyl nicotinate (EN), isopropyl nicotinate (IPN), butyl...