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Chemical Monthly

Current research reports and chronological list of recent articles..




The international scientific journal Chemical Monthly was originally conceived as an Austrian journal of chemistry, and has evolved into an international journal covering all branches of chemistry. It features the most recent research in analytical, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, including chemically oriented areas of biochemistry.

The publisher is Springer. The copyright and publishing rights of specialized products listed below are in this publishing house. This is also responsible for the content shown.

To search this web page for specific words type "Ctrl" + "F" on your keyboard (Command + "F" on a Mac). Then: type the word you are searching for in the window that pops up!

Additional research articles in the field of general chemistry, see Current Chemistry Research Articles. Magazines with similar content:

 - Angewandte Chemie International Edition,

 - Chemical Communications,

 - The Chemical Record,

 - Chemistry Central Journal,

 - Chemistry Letters,

 - Journal of the American Chemical Society,

 - Nature Chemistry.



Chemical Monthly - Abstracts



Theoretical study on the complexation of the hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate anions with dodecabenzylbambus[6] uril

Abstract

Applying quantum chemical calculations, the most likely conformations of the anionic complex species dodecabenzylbambus[6]uril–PF6, dodecabenzylbambus[6]uril–AsF6, and dodecabenzylbambus[6]uril–SbF6 were found. In all these complexes, the considered anions, incorporated in the ligand cavity, are bound by hydrogen bonds between methine hydrogen atoms on the convex face of glycoluril units of the dodecabenzylbambus[6]uril ligand and fluorine atoms of the respective “central” anion. Moreover, the interaction energies of the investigated three anionic complexes were calculated. The absolute values of these calculated energies increase in the series of SbF6 < AsF6 < PF6.

Graphic abstract


Datum: 28.03.2020


A simple adsorptive chronopotentiometric stripping method for determination of vitamin B 1 in pharmaceutical products

Abstract

A new electroanalytical method for vitamin B1 determination, based on adsorptive chronopotentiometric stripping analysis and non-specific adsorption onto mercury film electrode, was developed and validated. Stripping chronopotentiograms showed a single well-defined oxidation wave corresponding to vitamin B1 at about − 0.43 V in citrate buffer pH 6.0. The most important experimental factors affecting the monitored electroanalytical response of vitamin B1 were investigated and optimised. Under the optimal experimental conditions, linear response of vitamin B1 was obtained in the concentration range of 5–50 mg dm−3, with the achieved limit of detection of 1.64 mg dm−3, and the limit of quantitation of 4.97 mg dm−3. A mean recovery of 97.1% and relative standard deviations of 3.75% were achieved. The developed electrochemical procedure was successfully applied for the determination of vitamin B1 in pharmaceutical products. The results of the proposed method were in good agreement with those obtained by parallel HPLC analyses, confirming an accuracy of the developed method.

Graphic abstract


Datum: 28.03.2020


Green synthesis and antibacterial activity of chalcogenoesters

Abstract

Herein, we present a new variation for an eco-friendly methodology for the synthesis of chalcogenoester in good-to-excellent yields in a short time, with an easy work-up/purification step, and in a greenest methodology, affording the minimum generation of solid and liquid waste, in comparison to that described in the literature. Additionally, some selected compounds were evaluated as antimicrobial agents, showing moderate activity against a variety of microorganisms including the K. pneumoniae, P. aeruginosa and also some selected fish pathogenic bacteria.

Graphic abstract


Datum: 27.03.2020


Spectroscopic studies on the molecular interactions of curcumin and piperine

Abstract

The diarylheptanoid curcumin is the yellow coloring agent accumulated in the rhizome of the common spice turmeric (Curcuma longa L.). It has gathered a lot of pharmaceutical interest over the last decades due to some positive effects on human health. However, the use of curcumin as a drug is prevented by its low bioavailability and solubility in water. Interestingly, piperine, the pungent constituent of household pepper (Piper nigrum L.) is able to increase the bioavailability of curcumin up to 20-fold without any known adverse effects. The mechanism responsible for this piperine-based increase of curcumin bioavailability is, however, not fully understood. In a recent publication, a quantum chemical study suggested the formation of a molecular complex between curcumin and piperine being responsible for this effect. The present work now revealed that indeed a 1:1 complex formation can be observed in NMR titration experiments and by mass spectrometry, but the complex strength is rather low (K ~ 1.5 dm3/mol). Furthermore, it is shown that the presence of piperine does not increase the water solubility of curcumin, which makes it rather improbable that such a complex is the main reason for an enhanced curcumin bioavailability.

Graphic abstract


Datum: 27.03.2020


Adsorption property of congo red from aqueous solution by Cu-BTC/SiO 2 composite

Abstract

The adsorption behavior of congo red from aqueous solution on Cu-BTC/SiO2 was investigated. Cu-BTC/SiO2 with mesoporous structure and large surface area was prepared by loading Cu-BTC into the mesoporous silica using in-situ synthesis method. The X-ray diffraction, scanning electron microscopy, and nitrogen adsorption–desorption analysis were used to characterize the structure and morphology of the prepared materials. The adsorption studies showed that the adsorption isotherm of congo red on Cu-BTC/SiO2 fitted well with Freundlich adsorption model and congo red is easy to be adsorbed by Cu-BTC/SiO2. The thermodynamic study showed that the adsorption behavior of congo red on Cu-BTC/SiO2 is an exothermic process at temperature under investigation.

Graphic abstract


Datum: 26.03.2020


Co(II)-MOF for the chemical conversion of CO 2 and treatment effect on chronic enteritis by reducing the inflammatory response in HIEC

Abstract

This study presents a 3D metal–organic framework (MOF) material [Co2(atrz)2(bdc)]·(DMF)(H2O)2 based on Co(II) ions as the metal nodes. A three-substituted 1,2,4-triazole (Hatrz) was utilized as the functional unit in the reaction of 1,4-benzenedicarboxylate (H2bdc), Hatrz, and Co(NO3)2·6H2O in a mixed solvent of DMF and water. The high density of amino groups and abundant micropores (pore volume of 0.32 cm3/g and BET surface area of 764.5 m2/g) in solvent-free complex displayed good catalytic performance and substrate selectivity towards CO2 conversion under mild conditions due to the synergistic effects of the coordinatively unsaturated Co(II) sites. Furthermore, the protective function of the complex on chronic enteritis was assessed. ELISA assay was performed to detect the IL-18 and IL-1β released from human intestinal epithelial cells (HIEC) after compound treatment. Western blot was conducted to evaluate the activation of NLPR3–caspase-1 pathway in HIEC.

Graphic abstract


Datum: 26.03.2020


Graphene oxide and electropolymerized p -aminobenzenesulfonic acid mixed film used as dopamine and serotonin electrochemical sensor

Abstract

A novel electrochemical sensor is prepared by electropolymerization with p-aminobenzenesulfonic acid (p-ABSA) film and dropping graphene oxide on the surface of electrode. The results indicated that GO-poly(p-ABSA) nanofilms displayed enhanced current responses to dopamine and serotonin. In the range of 0.3–20 μmol dm−3 and 0.6–20 μmol dm−3, the dopamine and serotonin concentration are linearly related to current intensity, and the detection limit is 0.09 μmol dm−3 and 0.2 μmol dm−3 (S/N = 3), respectively. By adding dopamine and serotonin standards, the electrochemical sensor is applied in serum sample. The results show that the GO-poly(p-ABSA) films represent well-modified materials for use in the biosensors.

Graphic abstract


Datum: 26.03.2020


Ion recognition properties of new pyridine-2,6-dicarboxamide bearing propeller-like pendant residues: multi-spectroscopic approach

Abstract

The synthesis and ion binding properties of new amide derived from propeller-like tris(2-pyridyl)amine and 2,6-pyridinedicarboxylic acid chloride were described. Amide binds divalent metal cations: copper(II), nickel(II), zinc(II), and lead(II) in acetonitrile. In acetonitrile:water mixture (9:1 v/v) amide interacts only with copper(II) and nickel(II) cations forming complexes of 1:1 stoichiometry. It was found that the introduction of bulky, nitrogen donor atom bearing pendant groups can influence coordination mode of pyridine-2,6-dicarboxamides. The probable model of ligand-ion interactions is proposed on the basis of 1H NMR and FT-IR spectroscopy.

Graphic abstract


Datum: 12.03.2020


Synthesis of novel 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides as potent inhibitors of Mycobacterium tuberculosis

Abstract

A series of novel 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides was designed, synthesized, and evaluated for antitubercular activity. The required 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxylic acid intermediate was prepared by oxidizing the respective aldehyde with sodium chlorite and 30% H2O2. Further, the acid was coupled with various aryl, alkyl, and heterocyclic amines using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and hydroxybenzotriazole to give the desired 5-chloro-2-(thiophen-2-yl)-7,8-dihydroquinoline-6-carboxamides in excellent yields. All the new compounds were characterized by their NMR and mass spectral analysis. Screening of all new compounds for in vitro antimycobacterial activity against M. tuberculosis H37Rv (Mtb) resulted in five analogs with MIC 3.12 µg/cm3 as promising antitubercular agents with lower cytotoxicity profiles.

Graphic abstract


Datum: 12.03.2020


Synthesis and biological evaluation of new mono naphthalimide platinum(IV) derivatives as antitumor agents with dual DNA damage mechanism

Abstract

Naphthalimide has emerged as an interesting DNA intercalator and possessed attracting antitumor properties. In this context, naphthalimide group was linked to platinum(IV) core to construct a series of new mono naphthalimide platinum(IV) derivatives. The title compounds exert effective antitumor activities to the tested tumor cells lines in vitro, especially the one with propionyl chain displays comparable or even better bioactivities than platinum(II) reference drugs cisplatin and oxaliplatin. Moreover, the mono naphthalimide platinum(IV) derivative displays comparable tumor growth inhibitory competence against CT26 xenograft tumors in BALB/c mice in vivo without severe toxic effects in contrast to oxaliplatin. A dual DNA damage mechanism was proven for the title complex. Both naphthalimide ligand and the liberated platinum(II) moiety could generate DNA lesions to tumor cells synergistically and active the apoptotic pathway by up-regulating the expression of caspase 9 and caspase 3. Meanwhile, the conversion of platinum(II) drug into tetravalent form by incorporating naphthalimide moiety increases the uptake of platinum in whole cells and DNA remarkably. All these facts might be the factors for the title platinum(IV) complexes to overcome platinum(II) drug resistance. Additionally, the mono naphthalimide platinum(IV) complex could interact with human serum albumin by hydrogen bond and van der Waals force which would further influence their storage, transport and bioactivities.

Graphic abstract


Datum: 26.02.2020


Trimesic acid is a suitable building block in triple four-component Ugi reaction: access to unique trivalent compounds

Abstract

A triple four-component Ugi reaction of isocyanide, amine, aldehyde, and trimesic acid as the acid component with three acidic functional groups in MeOH at 65 °C has been disclosed. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of pharmacologically significant and structurally interesting compounds with several peptide groups, suitable for dendrimers and self-assembling. Substituents could be independently varied at three different positions. The structural assignments are supported by 1H and 13C NMR data.

Graphic abstract


Datum: 19.02.2020


A state-of-the-art approach to synthesis of dendrite-like gold nanostructures via electrodeposition

Abstract

Gold nanostructures such as nanoparticles, nanowires, or nanotubes are highly preferred structures in electrochemical studies and can be produced by electrodeposition. This study points out that the shapes and electrochemical behaviour of electrodeposited gold nanostructures can be varied by adjusting multi-walled carbon nanotube (MWCNT) ratio in electrodeposition solution. For that, gold nanofilms on the glassy carbon electrode surface were formed from HAuCl4 solution in the presence and absence of MWCNT. In this study, the gold concentration was fixed at 0.4 ppm (10.0 mM) and only MWCNT concentration was varied. The prepared electrode surfaces were characterized and compared with each other from the point of view of electrochemical, microscopic, and spectroscopic properties. Ultimately, it was shown that each prepared electrode had different properties.

Graphic abstract


Datum: 12.02.2020


Synthesis of 1,2,4-oxadiazole derivatives: anticancer and 3D QSAR studies

Abstract

A 3D QSAR study was performed on 1,2,4-oxadiazole derivatives using the [(SW) kNN MFA], CoMFA, and CoMSIA techniques. On the basis of 3D QSAR outcomes, new molecules were designed by substituting different substituents. These designed compounds were synthesized and confirmed their synthesis by spectroscopic techniques. The synthesized compounds were screened for their anticancer activity against different cancer cell lines. Compound 2-[3-(pyridine-4-yl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazole showed equipotent (IC50 = 4.96 μM) as 5-fluorouracil (IC50 = 3.2 μM) against colon (CaCo-2) cancer cell line, and compound [2-[3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazol-4-yl]methanol showed equipotent activity (IC50 = 0.35 μM) as compared to 5-fluorouracil (IC50 = 0.23 μM) against colorectal (DLD1) cancer cell line. Compound 2-[3-(3,4-dimethoxyphenyl)-1,2,4-oxadiazol-5-yl]benzo[d]thiazole was found to be 4–5 less potent (IC50 = 19.40 μM) as paclitaxel (IC50 = 4.10 μM) against breast (T47D) cancer cell line, and compound 4-[5-(benzo[d]thiazol-2-yl)-1,2,4-oxadiazol-3-yl]benzene-1,2-diol was found about 10 times less potent (IC50 = 15.7 μM) than mitomycin (IC50 = 1.50 μM) against prostate (PC-3) cancer cell line. These results disclose the discovery of new 1,2,4-oxadiazole-based anticancer drugs.

Graphic abstract


Datum: 12.02.2020


Simple and sensitive electrochemical determination of higenamine in dietary supplements using a disposable pencil graphite electrode

Abstract

In this study, a cheap, rapid, simple, and modification-free electroanalytical methodology based on the disposable pencil graphite electrode is described for the quantification of higenamine (isoquinoline-type alkaloid having three phenolic OHs). At first, the electrochemical oxidation of higenamine was investigated in aqueous solutions by cyclic voltammetry. The electrode process is pH-dependent and controlled by a mixture of diffusion and adsorption processes. Higenamine yielded two well-separated oxidation steps in acidic, neutral, and alkaline media by using square-wave voltammetry. By using the first oxidation peak due to its higher sensitivity, there was an excellent correlation between oxidation peak current at + 0.44 V and higenamine concentration (as hydrochloride salt) in the range of 0.05 to 2.0 μg cm−3 (1.63 × 10−7–6.5 × 10−6 mol dm−3), with a detection limit of 0.014 μg cm−3 (4.55 × 10−8 mol dm−3) in Britton–Robinson buffer at pH 4.0. As an example, the developed approach can be used for the quantification of higenamine in the commercial dietary supplement formulations.

Graphic abstract


Datum: 12.02.2020


The modifier action of NiO nanoparticles on the activity, structure, and stability of proteinase K

Abstract

In the present study, multi-spectroscopic methods were applied to investigate the effect of NiO nanoparticles on the structure, activity, and stability of proteinase K. To this aim, UV–Vis spectroscopy, circular dichroism photometry, and spectrofluorometry were conducted. UV absorption spectroscopy results revealed that with the addition of NiO nanoparticles, the maximum absorption of the enzyme showed hyperchromism. The regular decrement in the intrinsic fluorescence intensity of the enzyme was obtained with the increase in NiO nanoparticles concentrations. Far-circular dichroism also demonstrated a reduction in the β-sheet and β-turn and an increase in the α-helix content. Furthermore, the results obtained from this investigation revealed that the catalytic activity and thermal unfolding of the enzyme were improved in the presence of NiO nanoparticles in a concentration-dependent manner. Thus, NiO nanoparticles acted as an activator and stabilizer of proteinase K. Finally, the thermodynamic parameters showed that the enzyme–NiO nanoparticles combination was spontaneous and that the hydrophobic interactions and electrostatic forces played a key role in the interaction of the nanoparticles with the enzyme.

Graphic abstract


Datum: 05.02.2020


Synthesis, characterization, and thermal property of phosphate-based cobalt mixture of non-calcined, calcined, and composite material

Abstract

The phosphate-containing cobalt mixtures of non-calcined, calcined, and composite materials were synthesized in atmospheric conditions and characterized by different measurement techniques. Thermal study of these materials was carried out using DSC and TG–DTA techniques. From the study of thermal behaviour, it is observed that the composite material can not only be used as a sensible thermal heat storage material, but also can be used as a heat-dissipating material. The thermal behaviour of calcined mixture indicates its potential application towards use as a sensible thermal heat storage material due to its endothermic nature at high temperature. Average crystallite sizes were determined using the well-known Debye–Scherrer equation and are found to be 37.0 nm and 28.6 nm for the non-calcined and calcined mixture, respectively. The calculated band gap, Eg, of both the mixtures indicates their semiconducting behaviour at room temperature, and the calculated refractive index using the Moss and Ravindra relation are 2.52 and 2.62 for the non-calcined and calcined mixtures, respectively.

Graphic abstract


Datum: 01.02.2020


A catalytic multicomponent protocol to dihydropyridine-3-carboxylate from terminal alkynes, isocyanates, and malonates

Abstract

A domino catalytic reaction between terminal alkynes, isocyanates, and malonates has been developed. Copper acetylides attack on isocyanates to form a propargylic amide species which further reacted with malonates by the action of t-BuOLi to form dihydropyridine-3-carboxylates. The regioselectivity of the reaction has been examined with unsymmetrical malonate. The procedure is easy to implement, has a broad scope and allows the construction of the scaffolds by creating three covalent bonds in one pot.

Graphic abstract


Datum: 01.02.2020


Synthesis, in vitro antimicrobial assessment, and computational investigation of pharmacokinetic and bioactivity properties of novel trifluoromethylated compounds using in silico ADME and toxicity prediction tools

Abstract

1,3-Dipolar cycloaddition reactions of a sugar-based trifluoromethylated nitrone-to-maleimide and allyl bromide afforded a series of cycloadducts in good yield. The same nitrone reacts with propargyl acetate lead, after rearrangement of 4-isoxazoline, to aziridine with good yield. The obtained compounds were evaluated for their in vitro antimicrobial potency. Additionally, we are interested in predicting their physicochemical parameters such as lipophilicity and bioactivity score as well as their pharmacokinetic properties such as absorption, distribution, metabolism, and excretion (ADME) such as plasma protein binding (PPB) penetration of the blood–brain barrier (BBB), human intestinal absorption (HIA), cellular permeability (PCaco-2), cell permeability of Madin–Darby canine kidney (PMDCK), P-glycoprotein (P-gp) efflux, CYP inducers, substrates and inhibitors’ skin and permeability (PS), and their toxicological behavior [mutagenicity, carcinogenicity, acute, environmental, cardiotoxicity (hERG inhibition)] using in silico computational methods. Also, we aimed to validate QSAR models for the elucidation of their antitarget using 32 sets of end-points (IC50, Ki and Kact). The obtained result provides good information about the pharmacotherapy potential and toxicity of the examined molecules with good compliance between in vitro antimicrobial and the predicted properties. Findings indicated and encouraged the use of these compounds and their derivatives for further in vivo evaluations in the design and the elucidation of the intrinsic mechanisms as well as the efficacy of the selected powerful drug.

Graphic abstract


Datum: 01.02.2020


Investigation of photophysical and photochemical properties of phthalocyanines bearing fluorinated groups

Abstract

This study presents synthesis of novel peripherally tetrasubstituted Zn(II) and In(III) phthalocyanine complexes bearing 3,5-bis(trifluoromethyl)phenoxy groups. These phthalocyanines were characterized by performing elemental analysis, mass spectrometry, nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and ultraviolet visible spectrophotometric techniques. Aggregation properties of the resulting phthalocyanines were studied in different concentrations of DMSO. Aggregation behavior of the newly synthesized phthalocyanines was investigated in various organic solvents, as well. Photochemical and photophysical characterization of the resulting compounds were carried out to evaluate their photodynamic therapy properties in DMSO. The new metallophthalocyanines have high singlet oxygen quantum yields ranging from 0.72 to 0.88.

Graphic abstract


Datum: 01.02.2020


Formation of furo[3,2- c ]quinolone-2-carbonitriles and 4-oxo-4,5-dihydrofuro[3,2- c ]quinolone-2-carboxamides from reaction of quinoline-2,4-diones with 2-[bis(methylthio)methylene]malononitrile

Abstract

Quinoline-2,4-diones reacted with 2-[bis(methylthio)methylene]malononitrile in DMF/Et3N to produce 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carbonitriles and 3-(methylthio)-4-oxo-4,5-dihydrofuro[3,2-c]quinolone-2-carboxamides in state of 2-imino-substituted 4-(methylthio)-5,6-dihydro-2H-pyrano[3,2-c]quinolone-3-carbonitriles. The structures of all new products were proved using NMR, IR, and mass spectral data. The possible mechanism for the reaction is also discussed.

Graphic abstract


Datum: 01.02.2020


 


Category: Current Chemistry Research

Last update: 28.03.2018.






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