JSCS Vol 79, No 5

 

Whole issue - PDF  2,234 KB

J. Serb. Chem. Soc. 79 (5) 517–526 (2014)

UDC 547.568.1–36+542.813:57–188:615.281:615.281:615.276:615.27; JSCS–4603; doi: 10.2298/JSC130222103C; Original scientific paper

 

Synthesis and biological activity of hydroxycinnAMoyl- containing antiviral drugs

MAYA G. CHOCHKOVA, ASSYA P. GEORGIEVA, GALYA I. IVANOVA*, NADYA NIKOLOVA**, LUCHIA MUKOVA**, LUBOMIRA NIKOLAEVA-GLOMB** AND TSENKA S. MILKOVA

South-West University ‘‘Neofit Rilski”, Blagoevgrad, Bulgaria

*DepartAMento de Química, Faculdade de Ciências, Universidade do Porto, Porto, Portugal
**The Stephan Angeloff Institute of Microbiology, Bulgarian Academy of Sciences, Sofia, Bulgaria

 

(Received 22 February, revised 24 June, accepted 1 October 2013)

Seven N-hydroxycinnAMoyl AMides were synthesized by 1-[3-(dime­thylAMino)propyl]-3-ethylcarbodiimide/1-hydroxybenzotriazole (EDC/HOBt) coupling of the corresponding substituted cinnAMic acids (p-coumaric-, ferulic-, sinapic- and caffeic acids) with influenza antivirals (AMantadine, rimantadine and oseltAMivir). The DPPH (1,1-diphenyl-2-picrylhydrazyl) scavenging abi­lities and the inhibitory effect on mushroom tyrosinase activity (using L-tyro­sine as the substrate) were investigated in vitro. Amongst the synthesized com­pounds, N-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oseltAMivir (1) and N-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]rimantadine (4), containing a catechol moiety, exhibited the most potent DPPH radical-scavenging activity. Amide (1) also displayed tyrosinase inhibitory effect toward L-tyrosine as the substrate (≈50 %). The synthesized compounds were also investigated for their in vitro inhibitory acti­vity against the replication of influenza virus A (H3N2).

 

Keywords: N-hydroxycinnAMoylAMides; influenza antivirals; mushroom tyro­sinase; monophenolase activity; antioxidant activity; anti-influenza activity.

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J. Serb. Chem. Soc. 79 (5) 527–531 (2014)

UDC 547.226+547.261’587.51’49+542.913:54–732+537.5; JSCS–4604; doi: 10.2298/JSC130127140S; Short communication

 

SHORT COMMUNICATION

Iodine-mediated one-pot synthesis of 3-cyanocoumarins and 3-cyano-4-methylcoumarins

DINESH SHARMA and JAGDISH K. MAKRANDI*

Department of Chemistry, BRCM College of Engineering &AMp; Technology, Bahal-127028, India
*Department of Chemistry, Maharshi Dayanand University, Rohtak-124001, India

 

(Received 27 January, accepted 21 November 2013)

2-Hydroxybenzaldehydes 1a–e on reaction with malononitrile (2) in the presence of iodine as catalyst give 3-cyanocoumarins 3a–e in one step under thermal heating as well as under microwave irradiation. The latter conditions are much more efficient in terms of time (2–5 min) and yield as compared to the thermal conditions (2–2.5 h). Following a similar procedure, 3-cyano-4-methylcoumarins 3f–i were also prepared by the reaction of2-hydroxyacetophenones 1f–i with 2.

 

Keywords: 3-cyanocoumarin/3-cyano-4-methylcoumarin; malononitrile; iod­ine; microwave irradiation; one-pot reaction.

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J. Serb. Chem. Soc. 79 (5) 533–543 (2014)

UDC 547.918:546.28–31:54.183:53:577.15; JSCS–4605; doi: 10.2298/JSC131004154I; Original scientific paper

 

Immobilization of b-glucosidase onto a mesoporous silica support: physical adsorption and covalent binding of the enzyme

DARJANA Ž. IVETIĆ, VLADIMIR V. SRDIĆ and MIRJANA G. ANTOV

University of Novi Sad, Faculty of Technology, Bulevar cara Lazara 1, 21000 Novi Sad, Serbia

 

(Received 4 October, revised 20 December, accepted 27 December 2013)

In this study, the immobilization of β-glucosidase onto mesoporous silica support by physical adsorption and covalent binding was investigated. The immobilization was performed onto micro-sized silica aggregates with an average pore size of 29 nm. During physical adsorption, the highest yield of immobilized β-glucosidase was obtained with an initial protein concentration of 0.9 mg mL-1. The addition of NaCl increased 1.7-fold, while the addition of Triton X-100 decreased 6-fold adsorption yield in comparison to the one obtained without any addition. Covalently bonded β-glucosidase, via glutaral­dehyde previously bonded to silanized silica, had a higher yield of immobilized enzyme as well as higher activity and substrate affinity in comparison to the one physically adsorbed. Covalent binding did not considerably change pH and temperature stability of the obtained biocatalyst in range of values that are commonly used in reactions in comparison to the unbound enzyme. Further­more, covalent binding provided a biocatalyst that retained over 70 % of its activity after 10 cycles of reuse.

 

Keywords: β-glucosidase; immobilization; physical adsorption; chemical bind­ing; mesoporous silica.

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J. Serb. Chem. Soc. 79 (5) 545–556 (2014)

UDC 546.562+546.137:539.196:547.497+547.84; JSCS–4606; doi: 10.2298/JSC130910120M; Original scientific paper

 

Synthesis, characterization and crystal structure of Cu(II) complex with a diimine-dioxime ligand, [Cu₂(LH)₂](ClO₄)₂. Influence of the weak Cu×××O(perchlorate) interaction on the structure of the Cu₂N₂O₂ metallocycle

MARIJA MIRKOVIĆ, NADEŽDA NIKOLIĆ, DUŠAN MIJIN*, MILKA AVRAMOV IVIĆ**, AGNEŠ KAPOR*** and ZORAN D. TOMIĆ

Vinča Institute of Nuclear Sciences, University of Belgrade, P. O. Box 522, 11001 Belgrade, Serbia
*Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120 Belgrade, Serbia
**ICTM – Department of Electrochemistry, University of Belgrade, Njegoseva 12, Belgrade, Serbia

***Department of Physics, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000 Novi Sad, Serbia

 

(Received 10 September, revised 28 October, accepted 31 October 2013)

The diimine–dioxime ligand, 3,3¢-(1,4-butanediyl-dinitrilo)bis-2-pent­anone, 2,2¢-dioxime (LH2), containing a N4 donor set was prepared by the Schiff base condensation of 2-hydroxyimino-3-pentanone and 1,4-diAMino­butane in two ways: in a protic and in an aprotic solvent. A higher yield of the (LH2) imine was obtained when the synthesis was performed using a protic solvent (C2H5OH) instead of aprotic benzene (78 and 30 %, respectively). The Cu(II) metal complex of diimine–dioxime was synthesized in CH3OH from the perchlorate salt of LH2 in a 1:1 mole ratio. The isolated complex was character­ized by the elemental analysis, IR spectroscopy and cyclic voltAMmetry. The structure of [Cu2(LH)2](ClO4)2 was determined by single-crystal X-ray dif­fraction analysis. Comparison with structurally related diimine–dioxime Cu(II) complexes revealed the influence of a weak Cu…O(perchlorate) interaction on the geometry of the metallocycle.

 

Keywords: Cu(II) complex; weak interactions; suprAMolecular aggregates; diimine–dioxime ligand.

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J. Serb. Chem. Soc. 79 (5) 557–563 (2014)

UDC 544.112+532.74:544.131:515.12; JSCS–4607; doi: 10.2298/JSC130930001G; Original scientific paper

 

Relating the ABC and harmonic indices

IVAN GUTMAN, LINGPING ZHONG* and KEXIANG XU*

Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac, Serbia and Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia

*Department of Mathematics, Nanjing University of Aeronautics and Astronautics, Nanjing 210016, P. R. China

 

(Received 30 September, accepted 30 December 2013)

The atom–bond connectivity (ABC) index is a much-studied mole­cular structure descriptor, based on the degrees of the vertices of the molecular graph. Recently, another vertex–degree-based topological index, the harmonic index (H), has attracted attention and gained popularity. It is shown how ABC and H are related.

 

Keywords: topological index; degree-based topological index; atom–bond con­nectivity index; ABC index; harmonic index.

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J. Serb. Chem. Soc. 79 (5) 565–578 (2014)

UDC 546.56–71+547.576’288.3:547.261:547.84; JSCS–4608; doi: 10.2298/JSC130730137B; Original scientific paper

 

ThermodynAMics of the complexation between salicylaldehyde thiosemicarbazone with Cu(II) ions in methanol–1,4-dioxane binary solutions

RASHMIDIPTA BISWAS, DHIRAJ BRAHMAN and BISWAJIT SINHA

Department of Chemistry, University of North Bengal, Darjeeling-734013, India

 

(Received 30 July, revised 7 November, accepted 19 November 2013)

The complexation reaction between salicylaldehyde thiosemi­car­bazone, abbreviated as STSC, with Cu(II) ion was studied in binary mixtures of methanol–1,4-dioxane using UV–Vis spectrophotometric and conductometric methods at different temperatures. The formation constants (Kf) for the 1:1 complex, Cu(II)–STSC, were calculated from computer fitting of the absor­bance and molar conductance data against various concentrations ratios (cM:cL or cL:cM) in different binary solvent mixtures. A non-linear correlation was observed for the variation of log Kf for the complex against the solvent com­positions. Various thermodynAMic parAMeters (ΔH, ΔS and ΔG) for the for­mation of the Cu(II)–STSC complex were also determined from the tempe­rature dependence of the formation constants (Kf). The results showed that the complexation reaction is affected by the nature and composition of the mixed solvents.

 

Keywords: salicylaldehyde thiosemicarbazone; Cu(II); stability constants; bin­ary mixtures; methanol; 1,4-dioxane.

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J. Serb. Chem. Soc. 79 (5) 579–586 (2014)

UDC Cefotaxime+546.33+546.212:543.544.5.068.7; JSCS–4609; doi: 10.2298/JSC130821008S; Short communication

 

SHORT COMMUNICATION

Chromatographic analysis of immobilized cefotaxime

DANIELA STIRBET, SIMONA-CARMEN LITESCU* and GABRIEL-LUCIAN RADU

Department of Analytical Chemistry and Environmental Engineering, Faculty of Applied Chemistry and Material Sciences, “Politehnica” University of Bucharest, 1–7 Gheorghe Polizu, District 1, Bucharest-011061, Romania

*Centre of Bioanalysis, National Institute of Biological Sciences, Bucharest, 296 Splaiul Independentei, District 6, Bucharest-060031, Romania

 

(Received 21 August 2013, revised and accepted 22 January 2014)

Abstract: The aim of the present work was to widen the application of an
in-house developed fast, flexible and sensitive high performance liquid chro­ma­tography (HPLC) method to the assessment of cefotaxime sodium from aqueous sAMples. The method was applied to establish the release profile of cefotaxime sodium immobilised in MCM-41 nanoparticles using pH-controlled release in an aqueous medium. The analytical method proved to be sensitive, repeatable (RSD < 1.5 %) and reproducible (RSD < 1 %) in the studied concen­tration range (0.01–10 μg·mL-1). The limit of detection and limit of quantifi­cation were 0.036 and 0.12 μg·mL-1, respectively, suitable for the analysis of the release of a single active ingredient, and the analysis time was short (10 min).

 

Keywords: cefotaxime sodium; cephalosporins; controlled release; HPLC.

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J. Serb. Chem. Soc. 79 (5) 587–596 (2014)

UDC 677.4+547.295.94+546.33:66.065.5:678.742; JSCS–4610; doi: 10.2298/JSC130702150Z; Original scientific paper

 

Effect of polar additives on melt electrospinning of non-polar polypropylene

ZHIYUAN CHEN, JIANYUN HE, FENGWEN ZHAO, YUEXING LIU, YONG LIU and HUILIN YUAN*

College of Mechanical and Electrical Engineering, Beijing University of Chemical Technology, Beijing 100029, China

*College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China

 

(Received 2 July, revised 17 November, accepted 3 December 2013)

Melt or solution electrospinning are effective and direct techniques for producing nanoscale fibers. Polypropylene (PP) cannot be easily dissolved at AMbient temperature. Thus, it is commonly electrospun in the melt state. However, compared with solution electrospun fibers, melt electrospun PP fibers are more uneven and with larger diAMeters. In this study, to remedy this problem, polar additives, nAMely stearic acid and sodium stearate, were added into pure PP. The effects of the additives were investigated. The results showed that in contrast to those of pure PP, the fiber diAMeter of PP with 8 wt. % stearic acid was decreased by 69.3 % (from 5.4 to 1.6 μm). The smallest fiber diAMeter was 600 nm and the smallest average fiber diAMeter was 1.8 μm when the sodium stearate contents were 10 and 8 wt. %, respectively. The addition of polar compounds altered not only the diAMeters of PP microfibers, but also the distribution of diAMeters, the processing current, and even the thermal pro­perties of the fibers. The microcosmic mechanisms for these changes were interpreted.

 

Keywords: diAMeter; microfiber; non-polar polymer; sodium stearate; stearic acid; crystallization.

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J. Serb. Chem. Soc. 79 (5) 597–612 (2014)

UDC 547.99:627.8.034.7:665:628.5(282.243.742); JSCS–4611; doi: 10.2298/JSC130614087S; Original scientific paper

 

The use of biological markers in the determination of the origin and type of organic matter in the sediments of the Tisza River

SNEŽANA ŠTRBAC, GORDANA GAJICA*, ALEKSANDRA ŠAJNOVIĆ*, NEBOJŠA VASIĆ**, KSENIJA STOJANOVIĆ*** and BRANIMIR JOVANČIĆEVIĆ***

Faculty of Environmental Protection, University EDUCONS, Vojvode Putnika 87, 21207 Sremska KAMenica, Serbia

*University of Belgrade, ICTM, Center of Chemistry, Njegoševa 12, 11000 Belgrade, Serbia

**University of Belgrade, Faculty of Mining and Geology, Djušina 7, 1100 Belgrade, Serbia

***University of Belgrade, Faculty of Chemistry, Studentski trg 12–16, 11000 Belgrade, Serbia

 

(Received 14 June, revised 28 August, accepted 29 August 2013)

Abstract: The objective of this study was to determine the origin and type of organic matter (OM) in recent sediments of the Tisza River, along a distance of 153 km through the territory of Serbia. For this purpose, group organic–geo­chemical parAMeters and biomarker compositions were used. All sAMples con­tained approximately sAMe AMount of OM, which was deposited under uni­form, slightly reducing conditions. Based on the distribution of n-alkanes, the origin and type of OM could not be precisely estimated. However, the n-alkane patterns suggest the presence of immature singenetic organic matter of terres­trial origin. The distributions of terpanes and steranes and the values of the cor­responding maturity parAMeters indicate that the Tisza River sediments, apart from immature singenetic organic matter, contain oil pollutants of anthro­po­genic origin. The identical compositions of these biomarkers in all sAMples con­firmed that the recent sediments of the Tisza River, from Kanjiža Town to the confluence into the Danube River, contain the sAMe type of oil pollutants. Based on the compositions of terpanes and steranes and the values of the bio­marker parAMeters in Tisza sediments, it is supposed that the oil pollution generally could be related to heavy fuel oil from tankers, due to intense river transport and, to lower extent, to crude oils from the Elemir and Rusanda oil fields.

 

Keywords: sediments; Tisza River; organic matter; biomarkers; oil pollutants.

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J. Serb. Chem. Soc. 78 (5) 613–626 (2013)

UDC 664.111:66.011+544.6.076.32–034.1:66.087.5; JSCS–4612; doi: 10.2298/JSC130408074T; Original scientific paper

 

Optimization of electrocoagulation process to treat biologically pretreated bagasse effluent

KARICHAPPAN THIRUGNANASAMBANDHAM, VENKATACHALAM SIVAKUMAR and JEGANATHAN PRAKASH MARAN

Department of Food Technology, Kongu Engineering College, Perundurai, Erode-638052, TN, India

 

(Received 8 April, revised 24 June, accepted 27 June 2013)

The main objective of the present study was to investigate the effi­ciency of the electrocoagulation process as a post-treatment to treat biolo­gically pretreated bagasse effluent using iron electrodes. The removal of the chemical oxygen demand (COD) and the total suspended solids (TSS) were studied under different operating conditions, such as AMount of dilution, initial pH, applied current and electrolyte dose using the response surface metho­dology (RSM) coupled with a four-factor three-level Box–Behnken experi­mental design (BBD). The experimental results were analyzed by the Pareto analysis of variance (ANOVA) and second order polynomial mathematical models were developed with high correlation of efficiency (R2) for COD, TSS removal and electrical energy consumption (EEC). The individual and com­bined effects of the variables on the responses were studied using three dimen­sional response surface plots. Under the optimum operating conditions, i.e., AMount of dilution at 30 %, initial pH of 6.5, applied current of 8 mA cm-2 and electrolyte dose of 740 mg L-1, high removal efficiencies of COD (98 %) and TSS (93 %) were obtained with an EEC of 2.40 Wh, which were confirmed by validation experiments.

 

Keywords: electrocoagulation; iron electrode; post treatment; model develop­ment; optimization

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May 21. 2014.

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