Vol 77, No 10 - Abstracts

JSCS Vol 77, No. 10

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J. Serb. Chem. Soc. 77 (10) 1311–1338 (2012)

UDC 541.182+547.586.7+66.093+544.032.732+547.631’235.2; JSCS–4354; doi: 10.2298/JSC120713078D; Authors’ review

AUTHORS’ REVIEW

A comparative study of the linear solvation energy relationship for the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents

SAŠA Ž. DRMANIĆ, JASMINA B. NIKOLIĆ, ALEKSANDAR D. MARINKOVIĆ and BRATISLAV Ž. JOVANOVIĆ*

Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, Belgrade, Serbia

*Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, Belgrade, Serbia

(Received 13 July, revised 19 July 2012)

The effects of protic and aprotic solvents on the reactivity of picolinic, nicotinic and isonicotinic acid, as well as of some substituted nicotinic acids, with diazodiphenylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the exAMined acids with DDM were correlated using the CAMlet–Taft Solvatochromic Equation. The correlations of the kinetic data were realized by means of multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the coefficients of the Equation support the already known reaction mechanism. Solvation models for all the investigated acids are suggested and related to their specific structure.

Keywords: pyridine carboxylic acids; linear solvation energy relationship; diazodiphenylmethane; protic and aprotic solvents.

Full Article - PDF 375 KB Available OnLine: 12. 07. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1339–1344 (2012)

UDC 542.913+547.85+547.587.51+547.23–31; JSCS–4355; doi: 10.2298/JSC111024045M Original scientific paper

Synthesis of 2-azetidinones substituted coumarin derivatives

UDAY C. MASHELKAR, MUKESH S. JHA and BEENA U. MASHELKAR

Organic Research Laboratory, S. S. and L. S. Patkar College, Goregaon (West), Mumbai 400 062, India

(Received 24 October 2011, revised 5 April 2012)

α-Naphthol was converted into 4-methyl-2H-benzo[h]chromen-2-one by reacting with ethyl acetoacetate in the presence of bismuth trichloride. The product was oxidized to 2-oxo-2H-benzo[h]chromene-4-carbaldehyde and then condensed with aromatic primary AMines to give Schiff bases 3a–d. These Schiff bases were then reacted with acid chlorides in the presence of a base in toluene to give 1,3,4-substituted 2-azetidinones.

Keywords: α-naphthol; selenium dioxide; aromatic AMine; acid chloride; ethyl acetoacetate; tri-n-butylAMine; 2-azetidinone.

Full Article - PDF 179 KB Supplementary Material PDF 146 KB Available OnLine: 21. 05. 2011. Cited by

J. Serb. Chem. Soc. 77 (10) 1345–1352 (2012)

UDC 547.747+542.913+547.53:544.4:66–911.4+54.71; JSCS–4356; doi: 10.2298/JSC111211067J Original scientific paper

A clean and efficient L-proline-catalyzed synthesis of polysubstituted benzenes in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate

SHUBHA JAIN, BALWANT S. KESHWAL and DEEPIKA RAJGURU

School of Studies in Chemistry, VikrAM University, Ujjain, Madhya Pradesh-456010, India

(Received 11 December 2011, revised 20 June 2012)

A clean and efficient synthesis of polysubstituted benzenes has been developed via sequential vinylogous Michael addition and nucleophilic cyclization reactions of arylethylidenemalonodinitriles with arylidenemalonodinitriles in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) employing L-proline as a catalyst.

Keywords: polysubstituted benzenes; organocatalysis; ionic liquids; green chemistry.

Full Article - PDF 194 KB Supplementary Material PDF 158 KB Available OnLine: 01. 07. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1353–1361 (2012)

UDC 547.295.96+547.473:577.15+612.064:615.27; JSCS–4357; doi: 10.2298/JSC120105042S Original scientific paper

Anti-elastase, anti-urease and antioxidant activities of (3–13)-monohydroxyeicosanoic acid isomers

BAHAR BILGIN SOKMEN, HULYA CELIK ONAR*, AYSE YUSUFOGLU* and REFIYE YANARDAG**

Department of Chemistry, Faculty of Arts and Sciences, Giresun University, 28049, Giresun, Turkey

*Faculty of Engineering, Department of Chemistry, Organic Division, Istanbul University, Avcilar-Istanbul, 34320, Turkey

**Faculty of Engineering, Department of Chemistry, Biochemistry Division, Istanbul University, Avcilar-Istanbul, 34320, Turkey

(Received 5 January, revised 5 April 2012)

A series of (3–13)-monohydroxyeicosanoic acid isomers were evaluated for their anti-elastase, anti-urease and antioxidant activities for the first time in this study. All the test compounds exhibited anti-elastase, anti-urease and antioxidant activities. According to the obtained results, the hydroxyeicosanoic acid isomers in which the hydroxyl group is located in the middle or close to the middle of the chain showed higher anti-elastase, anti-urease and antioxidant activities than that of the other isomers. Therefore, (3–13)-monohydroxyeicosanoic acid isomers can be used in agriculture, pharmacy and cosmetic industries due to their excellent anti-elastase, anti-urease and antioxidant activities.

Keywords: anti-elastase; anti-urease; antioxidant; hydroxyeicosanoic acid; enzyme; inhibition.

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J. Serb. Chem. Soc. 77 (10) 1363–1379 (2012)

UDC *Leptosphaeria maculans:615.918:51.2:543.544.943.3.068.7; JSCS–4358; doi: 10.2298/JSC111231048M; Original scientific paper

Characterization of sirodesmins isolated from the phytopathogenic fungus Leptosphaeria maculans

PETAR M. MITROVIĆ, DEJAN Z. ORČIĆ*, ZVONIMIR O. SAKAČ, ANA M. MARJANOVIĆ-JEROMELA, NADA L. GRAHOVAC, DRAGO M. MILOŠEVIĆ**3 and DRAGANA P. MARISAVLJEVIĆ***

Institute of Field and Vegetable Crops, Maksima Gorkog 30, 21000 Novi Sad, Serbia

*University of Novi Sad, Faculty of Sciences, Dositeja Obradovića 3, 21000 Novi Sad, Serbia

**University of Kragujevac, Faculty of Agronomy, Cara Dušana 34, 32000 Čačak, Serbia

***Institute for Plant Protection and Environment, Teodora Drajzera 9, 11000 Belgrade, Serbia

(Received 31 December 2011, revised 10 April 2012)

The pathogenicity of phytopathogenic fungi is associated with phytotoxins, especially with their chemical nature and quantity. Sirodesmins are phytotoxins from the epipolythiodioxopiperazines group, produced by the fungus Leptosphaeria maculans, which are a cause of blackleg and stem canker in oilseed rape (Brassica napus L.). The aim of this work was to obtain a detailed chemical profile of sirodesmins in five fungal isolates (four from Vojvodina, Serbia and one from the UK). Sirodesmins showing different phytotoxicity on treated cotyledons of cv. Quinta were separated and detected by thin layer chromatography in all analysed isolates (L.m, C-3, St-5 and S-11) except K-113, which neither contained sirodesmin congeners nor did it exhibit activity. By use of high performance liquid chromatography coupled with tandem mass spectrometer, it was possible to identify total of 10 sirodesmins, together with their precursor – phomAMide. It was found that the dominant epipolythiodioxopiperazines of the investigated L. maculans isolates were sirodesmin PL, sirodesmin C, and their de-acetylated derivatives.

Keywords: epipolythiodioxopiperazine; thin layer chromatography; liquid chromatography; mass spectrometry; phytotoxicity.

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J. Serb. Chem. Soc. 77 (10) 1381–1389 (2012)

UDC 544.4.004.12+541.515:635.64+633.879.6; JSCS–4359; doi: 10.2298/JSC120410065S; Original scientific paper

Kinetic behaviour of the DPPH radical-scavenging activity of tomato waste extracts

SLADJANA M. SAVATOVIĆ, GORDANA S. ĆETKOVIĆ, JASNA M. ČANADANOVIĆ-BRUNET AND SONJA M. DJILAS

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

(Received 10 April, revised 16 June 2012)

The kinetic behaviour of tomato waste extracts (obtained from six genotypes) and standard antioxidant compounds (ascorbic and caffeic acid) were investigated using the 2,2-diphenyl-1-picrylhydrazyl radical test. Based on the time required for the reaction to reach steady state, the investigated extracts showed very slow (steady state ≥ 180 min) antiradical behaviour, ascorbic acid acted as a rapid antioxidant (steady state < 5min) while caffeic acid is a rapid–intermediate antioxidant (5 min < steady state < 20 min). The efficient concentrations at different kinetic times EC50,t were determined for all extracts, as well as for ascorbic and caffeic acid. The EC50,t was used as a parAMeter to screen and compare antiradical activites of food extracts with slow kinetic action. Irrespective of the time considered, a comparison of the EC50,t values for extracts of tomato waste obtained from different tomato genotypes showed that their DPPH radicals-scavenging activity decreased in the order O2 > Knjaz > Bačka > Saint Pierre > Rutgers > Novosadski niski. The tomato waste extracts showed very slow kinetic action, which is probably the result of the different kinetic bevaviour of the phenolic compounds present in tomato waste, as well as other antioxidants (vitAMins, carotenoids, etc.).

Keywords: tomato waste; DPPH radicals; free radical scavenger; kinetic behaviour.

Full Article - PDF 238 KB Available OnLine: 16. 09. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1391–1399 (2012)

UDC 546.732+546.482+547.269.3–165:54–77; JSCS–4360; doi: 10.2298/JSC120419051D; Original scientific paper

Cobalt(II) and cadmium(II) compounds with adAMantane-1-sulfonic acid

MILENA ĐORĐEVIĆ, DEJAN JEREMIĆ, KATARINA ANĐELKOVIĆ, MAJA GRUDEN-PAVLOVIĆ, VLADIMIR DIVJAKOVIĆ*, MAJA ŠUMAR RISTOVIĆ AND ILIJA BRČESKI

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

*Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 4, 21000 Novi Sad, Serbia

(Received 12 April, revised 11 May 2012)

In this work, the syntheses and characterization of two novel compounds of adAMantane-1-sulfonic acid (1-AdSO3H) with cobalt(II) and cadmium(II) are reported. The results of single crystal X-ray analysis of the compounds revealed that adAMantane-1-sulfonate (1-AdSO3-) in the monoanionic form plays different roles in the investigated compounds. NAMely, while in compound [Co(H2O)6](1-AdSO3)2, six water molecules are coordinated to the cobalt(II) ion and 1-AdSO3- serves as a counter ion, in compound [Cd(H2O)4(1-AdSO3)2], two molecules of 1-AdSO3- are trans-coordinated to the cadmium(II) ion as a monodentate (O)-ligand and the other coordination sites are occupied by water molecules. The obtained compounds showed moderate activity against Artemia salina.

Keywords: X-ray structure determination; transition metal compounds; metal complexes; adAMantane-1-sulfonate derivatives.

Full Article - PDF 606 KB Available OnLine: 22. 05. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1401–1408 (2012)

UDC 547.53:66–945.3+544.02+519.677; JSCS–4361; doi: 10.2298/JSC120518064G Original scientific paper

Verifying the modes of cyclic conjugation in tetrabenzo[bc,ef,op,rs]circumanthracene

IVAN GUTMAN, JELENA ĐURĐEVIĆ, ZORAN MATOVIĆ and MARIJA MARKOVIĆ

Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac, Serbia

(Received 19 May 2012)

Cyclic conjugation in the “empty” central ring of tetrabenzo[bc,ef,op,rs]circumanthracene (TBCA) is stronger than in its neighboring “non-empty” rings, contradicting the predictions of Kekulé-structure-based theoretical models. Earlier exAMples of such anomalous cyclic conjugation were observed in highly strained, non-planar benzenoid systems. As the molecule of TBCA is perfectly planar and strain-free, it was possible to test and verify its cyclic conjugation pattern by means of high-level, B3LYP/6-311+G(d,p), ab initio DFT calculations.

Keywords: cyclic conjugation; energy effect (of cyclic conjugation); Kekulé-structure-based models; DFT calculation; benzo-annelated perylene; tetrabenzocircumanthracene.

Full Article - PDF 379 KB Available OnLine: 19. 06. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1409–1422 (2012)

UDC 547.831+544.022+577.213.3+547.213.3+547.963.32+541.183; JSCS–4362; doi: 10.2298/JSC120420073R Original scientific paper

An electrochemical study of the adsorptive behaviour of varenicline and its interaction with DNA

VALENTINA RADULOVIĆ, MARA M. ALEKSIĆ* and VERA KAPETANOVIĆ

1University of Belgrade, Faculty of Pharmacy, Department of Analytical Chemistry, Vojvode Stepe 450, 11000 Belgrade, Serbia
*University of Belgrade, Faculty of Pharmacy, Department of Physical Chemistry and Instrumental Methods, Vojvode Stepe 450, 11000 Belgrade, Serbia

(Received 20 April, revised 10 July 2012)

The electrochemical behaviour of a novel nicotinic α4β2 subtype receptor partial agonist varenicline (VAR), which is used for smoking cessation, was investigated in Britton–Robinson buffers (pH 2.0–12.0) by cyclic, differential pulse and square wave voltAMmetry at a hanging mercury drop electrode (HMDE). The influence of pH, scan rate, concentration, accumulation potential and time on the peak current and potential suggested that the redox process was adsorption controlled in alkaline media. In addition, the experimental value of the surface coverage, G = 1.03×10-10 mol cm-2, was used to determine the conditions when VAR was fully adsorbed at the electrode surface. Bearing in mind the potential high toxicity of VAR due to the presence of a quinoxaline structure, its interaction with double stranded-DNA (ds-DNA) was postulated and studied when both compounds were in the adsorbed state at a modified HMDE. Using the adsorptive transfer technique, changes in potential and decreases in the normalized peak currents were observed. The estimated value of the ratio of surface-binding constants indicated that the reduced form of VAR interacted with ds-DNA more strongly than the oxidized form. Subtle DNA dAMage under conditions of direct DNA–VAR interaction at room temperature was observed. The proposed type of interaction was intercalation. This study employed a simple electroanalytical methodology and showed the potential of a DNA/ /HMDE biosensor for investigation of genotoxic effects.

Keywords: adsorption; DNA; interaction; varenicline; electrochemistry.

Full Article - PDF 286 KB Available OnLine: 10. 07. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1423–1436 (2012)

UDC *CarbAMazepine+543.544.5.068.7+577.121+611.018.5+66.061.34:616.853; JSCS–4363; doi: 10.2298/JSC120106084D; Original scientific paper

Development and validation of a solid phase extraction-HPLC method for the determination of carbAMazepine and its metabolites, carbAMazepine epoxide and carbAMazepine trans-diol, in plasma

PREDRAG DŽODIĆ, LJILJANA ŽIVANOVIĆ*, ANA PROTIĆ*, IVANA IVANOVIĆ**, RADMILA VELIČKOVIĆ-RADOVANOVIĆ, MIRJANA SPASIĆ, STEVO LUKIĆ and SLAVOLJUB ŽIVANOVIĆ

University of Niš, Faculty of Medicine, Bulevar dr Zorana Đinđića 81, 18000 Niš, Serbia

*University of Belgrade, Faculty of Pharmacy, Department of Drug Analysis, Vojvode Stepe 450, 11221 Belgrade, Serbia

**Avantor Performance Materials, Teugseweg 20, 7400 AA Deventer, The Netherlands

(Received 6 January, revised 11 June 2012)

A solid phase extraction-HPLC method has been developed and validated for the rapid analysis of carbAMazepine and its two metabolites, carbAMazepine epoxide and carbAMazepine trans-diol, in human plasma. The analysis was performed using a C18 Bakerbond-BDC analytical column (250 mm×4.6 mm i.d., particle size 5 μm). The optimal conditions for the separation were established with the mobile phase acetonitrile – 10 mM phosphate buffer, pH 7.0 (30:70, v/v) at a flow rate of 1.5 mL min-1 and temperature of 35 °C, with UV detection at 210 nm. The total run time was about 8 minutes. The SPE procedure for the extraction of the analytes from a plasma sAMple was developed using Oasis HLB cartridges and subsequently, the eluate was injected into the HPLC system for analysis. Afterwards, the SPE-HPLC method was subjected to validation. Linearity was obtained over the concentration range of 0.2–25 μg mL-1 for carbAMazepine, carbAMazepine epoxide and carbAMazepine trans-diol, with correlation coefficients higher than 0.995. The method showed good intra-day and inter-day precision with a relative standard deviation below 7.96 %, while the accuracy ranged from 92.09 to 108.5 % for all analytes. Finally, the method was successfully applied to the analysis of the plasma sAMples of epileptic patients in mono- and polytherapy.

Keywords: human plasma; carbAMazepine; carbAMazepine epoxide; carbAMazepine trans-diol; solid phase extraction.

Full Article - PDF 243 KB Supplementary Material PDF 227 KB Available OnLine: 10. 08. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1437–1442 (2012)

UDC 577.112.385+543.4/.5+543.23:546.562+546.215:615; JSCS–4364; doi: 10.2298/JSC120131079C; Note

NOTE

Determination of lisinopril in pharmaceuticals by a kinetic spectrophotometric method

MIRA ČAKAR and GORDANA POPOVIĆ

Faculty of Pharmacy, University of Belgrade, P. O. Box 146, Vojvode Stepe 450, 11000 Belgrade, Serbia

(Received 31 January, revised 23 July 2012)

A kinetic spectrophotometric method for determination of lisinopril in pharmaceuticals has been developed. The method is based on the activator action of lisinopril on Cu(II) ions catalysing the oxidation of Nile Blue A with hydrogen peroxide in borate buffer (pH 9.3). A decrease of the absorbance was recorded at 635 nm after 5 min at 25 °C. Linearity was established by application of the tangent method within the concentration range of lisinopril from 0.8–6.4 μg mL-1, the detection and quantification limits being 0.158 and 0.480 μg mL-1, respectively. The method was successfully applied to three brands of tablets containing lisinopril alone or in combination with hydrochlorothiazide.

Keywords: lisinopril; Nile Blue A; spectrophotometry; kinetic determination; pharmaceuticals.

Full Article - PDF 180 KB Available OnLine: 19. 03. 2012. Cited by

J. Serb. Chem. Soc. 77 (10) 1443–1456 (2012)

UDC 547.587.51:544.722.123+544.022:615.9; JSCS–4365; doi: 10.2298/JSC120716091R; Original scientific paper

Quantitative structure–toxicity relationship study of some natural and synthetic coumarins using retention parAMeters

EL HADI M. A. RABTTI, MAJA M. NATIĆ, DUŠANKA M. MILOJKOVIĆ-OPSENICA, JELENA Đ. TRIFKOVIĆ, TOMISLAV TOSTI, IVAN M. VUČKOVIĆ, VLATKA VAJS* and ŽIVOSLAV Lj. TEŠIĆ

Faculty of Chemistry, University of Belgrade, P. O. Box 51, 11158 Belgrade, Serbia

*Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia

(Received 16 July, revised 6 September 2012)

Four lipophilicity descriptors (RM0, b, C0 and PC1) for twelve coumarin derivatives were determined by reversed-phase thin-layer chromatography in order to analyze the descriptor which best describes the lipophilicity of the investigated coumarins. Moreover, possible chemical toxicity of coumarins, expressed as the probability of a compound to cause organ-specific health effects, was calculated using ACD/Tox Suite progrAM. The quantitative relationships between toxicity and molecular descriptors, including experimentally determined lipophilicity descriptors obtained in current study were investigated using partial least square regression. The best models were obtained for kidney and liver health effects. Quantitative structure–toxicity relationship models revealed the importance of electric polarization descriptors, size descriptors and lipophilicity descriptors. The obtained models were used for the selection of the structural features of the compounds that are significantly affecting their absorption, distribution, metabolism, excretion and toxicity.

Keywords: lipophilicity parAMeters; thin-layer chromatography; toxicity; partial least squares regression.

Full Article - PDF 244 KB Supplementary Material PDF 1,980 KB Available OnLine: 12. 09. 2011. Cited by

J. Serb. Chem. Soc. 77 (10) 1457–1481 (2012)

UDC 542.913:678.652+678.04+66.09+66.011:536.5.004.12; JSCS–4366; doi: 10.2298/JSC111025056B; Original scientific paper

The effect of polar solvents on the synthesis of poly(urethane–urea–siloxane)s

MILICA BALABAN, VESNA ANTIĆ*, MARIJA PERGAL**, IOLANDA FRANCOLINI***, ANDREA MARTINELLI*** and JASNA DJONLAGIĆ****

University of Banja Luka, Faculty of Science, Bosnia and Herzegovina

*University of Belgrade, Faculty of Agriculture, Serbia

**University of Belgrade, Institute of Chemistry, Technology and Metallurgy, Serbia

***University of Rome “Sapienza”, Dept. of Chemistry, Italy

****University of Belgrade, Faculty of Technology and Metallurgy, Serbia

(Received 25 October 2011, revised 9 April 2012)

Segmented poly(urethane–urea–siloxanes) (PUUS) based on 4,4′-methylene diphenyl diisocyanate–ethylene diAMine (MDI–ED) hard segments and hydroxypropyl-terminated poly(dimethylsiloxane) (PDMS, M̅n = 1000 g mol-1) soft segments were prepared under various experimental conditions. The copolymers with constant molar ratio of hard and soft segments (PDMS:MDI:ED = 1:2:1; 20 wt. % of the hard segments) were synthesized in two different solvent mixtures, by a two-step polyaddition procedure. The first one was tetrahydrofuran/N,N-dimethylacetAMide (THF/DMAc) with different co-solvent ratios (1/1, 1/2 and 1/9, v/v), whereas the second one was tetrahydrofuran/N-methylpyrrolidone (THF/NMP, 1/9, v/v). The reaction conditions were optimized by varying the co-solvents ratio, the concentration of the catalyst, the initial monomer concentration, as well as the time of the first and the second step of the reaction. The effects of the experimental conditions on the size of the PUUS were investigated by gel permeation chromatography (GPC) and dilute solution viscometry. The copolymers with the highest molecular weights were obtained in the THF/NMP mixture (1/9, v/v). The structure and composition of the copolymers were determined by 1H-NMR and FTIR spectroscopy. The morphology of the synthesized copolymers was investigated by atomic force microscopy (AFM), while the thermal properties were studied by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The surface properties were evaluated by measuring the water contact angle (WCA). The copolymers exhibited phase-separated microstructure and were stable up to 200 °C in nitrogen.

Keywords: urethane–urea–siloxane copolymers; two-step polyaddition; reaction conditions; optimization; thermal properties; microphase separation.

Full Article - PDF 877 KB Available OnLine: 04. 04. 2012. Cited by

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