Vol 76, No 9 - Abstracts

JSCS Vol 76, No. 9

Whole issue - PDF 2,492 KB

J. Serb. Chem. Soc. 76 (9) 1191–1198 (2011)

UDC 547.864+547.856+542.913:544.478; JSCS–4195; doi: 10.2298/JSC100801104K; Original scientific paper

A facile synthesis of phenazine and quinoxaline derivatives using magnesium sulfate heptahydrate as a catalyst

BAHADOR KARAMI and SAEED KHODABAKHSHI

Department of Chemistry, Yasouj University, Yasouj, zip code: 75918-74831, P. O. Box 353, Iran

(Received 1 August, revised 29 November 2010)

Convenient and simple procedures for the synthesis of phenazine and quinoxaline derivatives were developed via a reaction of o-phenylenediAMines and 1,2-dicarbonyl compounds. In addition, the synthesis of two new 1,4-benzodiazine derivatives and the catalytic activity of magnesium sulfate heptahydrate (MgSO₄·7H₂O) in the room temperature condensation of o-phenylenediAMines and 1,2-dicarbonyl compounds in ethanol as solvent are reported. This method has many appealing attributes, such as excellent yields, short reaction times, and simple work-up procedures.

Keywords: phenazine; quinoxaline; magnesium sulfate heptahydrate; catalyst.

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J. Serb. Chem. Soc. 76 (9) 1199–1206 (2011)

UDC 547.7+547.53–327+547.831+542.913:615.28–188; JSCS–4196; doi: 10.2298/JSC100817105C; Original scientific paper

Synthesis and antimicrobial activities of novel 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinolines

RAJU B. CHAUDHARI and SAHEBRAO S. RINDHE

PG Department of Chemistry; New Arts, Commerce and Science College, Ahmednagar-414003, Maharashtra, India

(Received 8 July 2010, revised 7 January 2011)

The synthesis of a series of novel 8-(1-alkyl/alkylsulphonyl/alkoxycarbonyl-benzimidazol-2-ylmethoxy)-5-chloroquinoline derivatives is reported. These derivatives were prepared by the condensation of o-phenylenediAMine with [(5-chloroquinolin-8-yl)oxy]acetic acid, followed by substitution at nitrogen with different electrophilic reagents in presence of an appropriate base to give a series of nitrogen heterocycles containing the benzimidazole and quinoline nuclei. The structures of the compounds were confirmed based on ¹H-NMR, ¹³C-NMR, IR and mass spectral data. Almost all the compounds exhibited promising antibacterial activity against Salmonella typhimurium and Staphylococcus aureus. Some of the compounds showed good antifungal activities against Aspergillus niger but the antifungal activities against Candida albicans were disappointing.

Keywords: heterocyclic; benzimidazole; quinoline; antibacterial; antifungal.

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J. Serb. Chem. Soc. 76 (9) 1207–1218 (2011)

UDC 633.852.73+581.45+66.094.3+591.4:611.33/.36; JSCS–4197; doi: 10.2298/JSC110204107D; Original scientific paper

Olive leaf extract modulates cold restraint stress-induced oxidative changes in rat liver

DRAGANA DEKANSKI, SLAVICA RISTIĆ, NEVENA V. RADONJIĆ*, NATAŠA D. PETRONIJEVIĆ*, ALEKSANDAR DEKANSKI** and DUŠAN M. MITROVIĆ***

Biomedical Research, R&AMp;D Institute, Galenika a.d., Belgrade, Serbia

*Institute for Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Serbia

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

***Institute for Medical Physiology “Richard Burian”, School of Medicine, University of Belgrade, Serbia

(Received 4 February, revised 18 March 2011)

Recently, the beneficial effects of different single doses of standardized dry olive (Olea europaea L.) leaf extract (OLE) in cold restraint stress (CRS)-induced gastric lesions in rats and its influence on oxidative parAMeters in gastric mucosa were demonstrated. The present study was undertaken to investigate the long-term pretreatment efficacy of OLE and its potential in the modulation of CRS-induced oxidative changes at the liver level. The experimental animals were divided into four groups, i.e., control, OLE-treated, CRS non-treated and CRS treated with OLE (CRS+OLE) groups. CRS caused severe gastric lesions in all non-pretreated animals and two-week pretreatment with OLE (80 mg per kg of body weight) attenuated stress-induced gastric lesions significantly. The malondialdehyde (MDA) level as an index of lipid peroxidation, superoxide dismutase (SOD) and catalase (CAT) activities were measured spectrophotometrically in liver tissue homogenates. The MDA level was increased in the CRS group and significantly decreased in the CRS+OLE group. The SOD and CAT activities were significantly decreased in the CRS group. In the CRS+OLE group, the activities of these two enzymes were significantly increased in comparison with the CRS group. The results obtained indicate that long-term supplementation with OLE provides oxidant/antioxidant balance in liver during stress condition.

Keywords: olive leaf; cold restraint stress; oxidative stress; liver

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J. Serb. Chem. Soc. 76 (9) 1219–1228 (2011)

UDC 663.551.5:634.23+543.544.3+543.51:54.004.12; JSCS–4198; doi: 10.2298/JSC101201109N; Original scientific paper

The effects of the cherry variety on the chemical and sensorial characteristics of cherry brandy

Ninoslav NIKIĆEVIĆ, Milovan VELIČKOVIĆ, Milka JADRANIN*, Ivan VUČKOVIĆ**, Miroslav NOVAKOVIĆ*, LJubodrag VUJISIĆ**, Miroslava STANKOVIĆ*, Ivan UROŠEVIĆ and Vele TEŠEVIĆ**

Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Zemun, Serbia

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

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

(Received 1 December 2010, revised 24 February 2011)

The chemical and sensorial characteristics of cherry brandy produced from five cherry varieties (Oblacinska, Celery’s 16, Rexle, Heiman’s Ruby and Heiman’s Conserve) grown in Serbia were studied. Gas chromatography and gas chromatography–mass spectrometry analysis of these distillates led to the identification of 32 components, including 20 esters, benzaldehyde, 6 terpenes and 5 acids. The ethyl esters of C₈–C₁₈ acids were the most abundant in all sAMples. The benzaldehyde content was quantified by high performance liquid chromatography with UV detection. The average benzaldehyde concentration in the sAMples ranged between 2.1 and 24.1 mg L^-1. The total sensory scores of the cherry brandies ranged between 17.30 to 18.05, with the cherry brandy produced from the Celery’s 16 variety receiving the highest score (18.05).

Keywords: aroma; benzaldehyde; cherry brandy; GC/MS; cherry varieties.

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J. Serb. Chem. Soc. 76 (9) 1229–1236 (2011)

UDC 577.112.384:633.71+633.12:576; JSCS–4199; doi: 10.2298/JSC110120106M; Original scientific pape

Cell wall localization of the aspartic proteinase from buckwheat (FeAPL1) over-expressed in tobacco BY-2 cells

MIRA Đ. MILISAVLJEVIĆ, GORDANA S. TIMOTIJEVIĆ, DRAGANA B. NIKOLIĆ, JELENA T. SAMARDŽIĆ and VESNA R. MAKSIMOVIĆ

Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, P. O. Box 23, 11010 Belgrade, Serbia

(Received 20 January, revised 24 March 2011)

The recombinant aspartic proteinase-like protein (FeAPL1-His₆) was overexpressed in the tobacco BY-2 cell line and the expected pepstatin A-sensitive enzymatic activity was confirmed at pH 3.0. Immunocytochemistry and protein gel blot analysis of the transformed BY-2 cells and their protoplasts showed extracellular localization of rFeAPL1-His₆ in the cell wall. Based on the obtained results, potential functions of FeAPL1 are discussed.

Keywords: aspartic proteinase; buckwheat; BY-2 cells; cell wall.

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J. Serb. Chem. Soc. 76 (9) 1237–1246 (2011)

547.484.7:57–188:546.302; JSCS–4200; doi: 10.2298/JSC100531108P; Original scientific paper

Synthesis, spectral, thermal and biological studies of transition metal complexes of 4-hydroxy-3-[3-(4-hydroxyphenyl)-acryloyl]-6-methyl-2H-pyran-2-one

VAIBHAV N. PATANGE and BALASAHEB R. ARBAD*

Department of Chemistry, Research and P. G. Center, Shri Chhatrapati Shivaji College, Omerga, Dist-Osmanabad-413606, Maharashtra, India

*Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004, Maharashtra, India

(Received 31 May 2010, revised 4 March 2011)

The solid complexes of Mn(II), Fe(III), Co(II), Ni(II), and Cu(II) with 4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-6-methyl-2H-pyran-2-one, derived from 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione (dehydroacetic acid) and 4-hydroxybenzaldehyde, were synthesized and characterized by elemental analysis, conductometry, thermal analysis, magnetic measurements, IR, ¹H-NMR and UV–Vis spectroscopy and a biological study. From the analytical and spectral data, the stoichiometry of the complexes was found to be 1:2 (metal:ligand). The physico–chemical data suggest a distorted octahedral geometry for the Cu(II) complexes and an octahedral geometry for all the other complexes. The thermal decomposition of all the complexes was studied by the TG–DTA method. The synthesized ligand and its metal complexes were screened for their in vitro antibacterial activity against GrAM-negative (Escherichia coli) and GrAM-positive (Staphylococcus aureus) bacterial strains and for in vitro antifungal activity against Aspergillus flavus, Curvularia lunata and Penicillium notatum. The results of these studies showed the metal complexes to be more antibacterial/antifungal against one or more species as compared with the non-complexed ligand.

Keywords: dehydroacetic acid; biological activity; transition metal complexes.

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J. Serb. Chem. Soc. 76 (9) 1247–1262 (2011)

UDC 66.011:663.991+577.354.3:543.544.164; JSCS–4201; doi: 10.2298/JSC110120110S; Original scientific paper

Modeling the ligand specific m- and d-opioid receptor conformations

MILAN SENĆANSKI, MILOVAN D. IVANOVIĆ*, SONJA VUČKOVIĆ** and LJILJANA DOŠEN-MIĆOVIĆ*

Innovation Center of the Faculty of Chemistry, University of Belgrade, Serbia

*Faculty of Chemistry, University of Belgrade and Center for Chemistry, ICTM, Studentski trg 12–16, P. O. Box 51, 11158 Belgrade, Serbia

**Department of Pharmacology, Clinical Pharmacology and Toxicology, School of Medicine, University of Belgrade, Belgrade, Serbia

(Received 20 January 2011)

An automated docking procedure was applied to study the binding of a series of m- and d-selective ligands to ligand-specific m- and d-opioid receptor models. Short-time molecular dynAMic simulations were used to obtain ligand-specific m- and d-opioid receptors from arbitrarily chosen models of the active form of these receptors. The quality of receptor model depended on the molecular volume of the ligand in the receptor–ligand complex used in the molecular dynAMic simulations. Within a series of ligands of similar size (volume), the results of ligand docking to the obtained ligand–specific receptor conformation were in agreement with point mutation studies. The correlation of the calculated and the experimentally determined binding energies was improved in relation to the initial receptor conformation.

Keywords: molecular modeling; opioid receptor; ligand–receptor interactions; docking simulation.

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J. Serb. Chem. Soc. 76 (9) 1263–1282 (2011)

UDC 66.011+54.061/.062:635.71:615.277; JSCS–4202; doi: 10.2298/JSC111227111B; Original scientific paper

Molecular modeling and chemometric study of anticancer derivatives of artemisinin

JARDEL P. BARBOSA, JOÃO E. V. FERREIRA, ANTONIO F. FIGUEIREDO, RUTH C. O. ALMEIDA, OSMARINA P. P. SILVA, JOSÉ R. C. CARVALHO, MARIA DA G. G. CRISTINO, JOSE CIRÍACO-PINHEIRO, JOSÉ L. F. VIEIRA*and RAYMONY T. A. SERRA**

Laboratório de Química Teórica e Computacional, Faculdade de Química, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, CP 101101, CEP 66075-110 Belém, PA, Amazônia, Brasil

*Faculdade de Farmácia, Instituto de Ciências da Saúde, Universidade Federal do Pará, CP 101101, CEP 6075-110 Belém, PA, Brasi

**Centro de Ciências Biológicas e da Saúde, Universidade Federal do Maranhão, CEP 65085-580 São Luis, MA, Brasil

(Received 27 December 2010)

In this work, a molecular modeling and multivariate study involving artemisinin and 28 derivatives with activity against human hepatocellular carcinoma HepG2 is reported. The studied calculations of the compounds were performed at the B3LYP/6-31G^** level. MEP maps were used in an attempt to identify key structural features of artemisinin and its derivatives that are necessary for their activities, and to investigate their interaction with the transferrin. The chemometrics methods PCA, HCA, KNN, SIMCA and SDA were employed in order to reduce dimensionality and to investigate which subset of variables could be more effective for classification of the compounds according to their degree of anticancer activity. Chemometric studies revealed that the ALOGPS_logs, Mor29m, IC5 and the gap energy descriptors are responsible for the separation into more active and less active compounds. In addition, molecular docking was used to investigate the interaction between ligands and receptor. The results showed that the ligands approached the receptor through the endoperoxide bond.

Keywords: artemisinin; HepG2; MEP maps; chemometrics; molecular docking.

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J. Serb. Chem. Soc. 76 (9) 1283–1294 (2011)

UDC 546.26–037:54–188:544.723.2:543.552; JSCS–4203; doi: 10.2298/JSC100226112K; Original scientific paper

Influence of chemical agents on the surface area and porosity of active carbon hollow fibers

LJILJANA M. KLJAJEVIĆ, VLADISLAVA M. JOVANOVIĆ*, SANJA I. STEVANOVIĆ*, ŽARKO D. BOGDANOV and BRANKA V. KALUDJEROVIĆ

University of Belgrade, Vinča Institute of Nuclear Sciences, P. O. Box 522, 11001 Belgrade, Serbia

*ICTM – Institute of Electrochemistry, University of Belgrade, P. O. Box 473, 11000 Belgrade, Serbia

(Received 26 February 2010, revised 31 May 2011)

Active carbon hollow fibers were prepared from regenerated polysulfone hollow fibers by chemical activation using: disodium hydrogen phosphate 2-hydrate, disodium tetraborate 10-hydrate, hydrogen peroxide, and diAMmonium hydrogen phosphate. After chemical activation fibers were carbonized in an inert atmosphere. The specific surface area and porosity of obtained carbons were studied by nitrogen adsorption–desorption isotherms at 77 K, while the structures were exAMined with scanning electron microscopy and X-ray diffraction. The activation process increases these adsorption properties of fibers being more pronounced for active carbon fibers obtained with disodium tetraborate 10-hydrate and hydrogen peroxide as activator. The obtained active hollow carbons are microporous with different pore size distribution. Chemical activation with phosphates produces active carbon material with small surface area but with both mesopores and micropores. X-ray diffraction shows that besides turbostratic structure typical for carbon materials, there are some peaks which indicate some intermediate reaction products when sodium salts were used as activating agent. Based on data from the electrochemical measurements the activity and porosity of the active fibers depend strongly on the oxidizing agent applied.

Keywords: carbon hollow fibers; chemical activation; adsorption; cyclic voltAMmetry.

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J. Serb. Chem. Soc. 76 (9) 1295–1305 (2011)

UDC 543.554+681.586.74:544.6.076.32–034.669+66.081; JSCS–4204; doi: 10.2298/JSC100826114A; Original scientific paper

A lutetium PVC membrane sensor based on (2-oxo-1,2--diphenylethylidene)-N-phenylhydrazinecarbothioAMide

HASSAN ALI ZAMANI, MOHAMMAD REZA GANJALI* and FARNOUSH FARIDBOD**

Department of Applied Chemistry, Quchan Branch, IslAMic Azad University, Quchan, Iran

*Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehra, Iran

**Endocrinology &AMp; Metabolism Research Center, Tehran University of Medical Sciences, Tehran, Iran

(Received 26 August, revised 18 November 2010)

Based on the former experience on the design and construction of metal ions sensors, especially those of high sensitivity for lanthanides, (2-oxo-1,2-diphenylethylidene)-N-phenylhydrazinecarbothioAMide (PHCT) was used to construct a Lu³⁺ PVC sensor exhibiting a Nernstian slope of 19.8±0.3 mV dec^-1. The sensor was found to function well over a concentration range of 1.0×10^-2 and 1.0×10^-6mol L^-1 of the target ion with a detection limit of 6.8×10^-7 mol L^-1. The sensor selectivity against many common alkaline, alkaline earth, transition, heavy metals and specially lanthanide ions was very good and it functioned well in the pH range 2.5–8.7. Having a lifetime of at least 2 months and a short response time of ≈ 5 s, the sensor was successfully used as an indicator electrode in the potentiometric titration of Lu³⁺.

Keywords: potentiometry; sensor; PVC membrane; ion-selective electrode.

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J. Serb. Chem. Soc. 76 (9) 1307–1323 (2011)

UDC 615.463+615.464:543.544.5.068.7+543.21:616.314; JSCS–4205; doi: 10.2298/JSC100610113O; Original scientific paper

Correlation between the degree of conversion and the elution of leachable components from dental resin-based cements

KOSOVKA OBRADOVIć-DJURIčIć, VESNA MEDIć, MARINA RADIšIć* and MILA LAUšEVIĆ*

Clinic for Prosthetic Dentistry, Faculty of Dentistry, University of Belgrade, Rankeova 4, 11000 Belgrade, Serbia

*Department of Analytical Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11120 Belgrade, Serbia

(Received 10 June 2010, revised 20 February 2011)

This study exAMined the possible correlation between the degree of conversion (DC) and the AMount of substances eluted from three commercial cured resin-based cements. The DC of the various resin-based cements was measured by RAMan spectroscopy, while the quantity of unreacted monomers released from the cement matrix (triethylene glycol dimethacrylate, TEGDMA, urethane dimethacrylate, UDMA, 2-hydroxyethyl methacrylate, HEMA and bisphenol A) was determined by high pressure liquid chromatography (HPLC). The obtained results, after multiple statistical evaluation (one way ANOVA, LSD post hoc test), showed no significant differences in the DC values between the resin cements. On the contrary, the results of the HPLC analysis depicted statistically significant differences between the three materials with respect to the AMount of leached monomers. In addition, no correlation between the DC and the AMount of eluted substances from the tested cured composite cements was found.

Keywords: dental resin-based cement; degree of conversion; eluted monomer.

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J. Serb. Chem. Soc. 76 (9) 1325–1336 (2011)

UDC 546.562+546.817+547.581.2+547.587.11+547.992:544.726; JSCS–4206; doi: 10.2298/JSC110310115K; Original scientific paper

Copper(II) and lead(II) complexation by humic acid and humic-like ligands

IVANA KOSTIĆ, TATJANA ANĐELKOVIĆ, RUŽICA NIKOLIĆ, ALEKSANDAR BOJIĆ, MILOVAN PURENOVIĆ, SRĐAN BLAGOJEVIĆ*and DARKO ANĐELKOVIĆ**

Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia

*Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Zemun, Serbia

**Water Work Association “Naissus”, Kneginje Ljubice 1/1, 18000 Niš, Serbia

(Received 10 March, revised 2 July 2011)

The stability of metal–humate complexes is an important factor determining and predicting speciation, mobility and bioavailability of heavy metals in the environment. A comparative investigation of the complexation of Cu(II) and Pb(II) with humic acid and humic-like ligands, such as benzoic and salicylic acid, was performed. The analysis was realized at pH 4.0, a temperature of 25 °C and at an ionic strength of 0.01 mol dm-3 (NaCl) using the Schubert ion-exchange method and its modified form. The stability constants were calculated from the experimental data by the Schubert method for complexes with benzoic and humic acid. A modified Schubert method was used for the determination of the stability constants of the complexes with salicylic acid. It was found that Cu(II) and Pb(II) form mononuclear complexes with benzoic and humic acid while with salicylic acid both metals form polynuclear complexes. The results indicate that Pb(II) has a higher binding ability than Cu(II) to all the investigated ligands. The Cu(II)–salicylate and Pb(II)–salicylate complexes showed noticeable higher stability constants compared with their complexes with humic acid, while the stabilities of the complexes with benzoic acid differed less. Salicylic and benzoic acids as humic-like ligands can be used for setting the range of stability constants of humic complexes with Cu(II) and Pb(II).

Keywords: copper; lead; benzoic acid; salicylic acid; humic acid; Schubert’s method.

Full Article - PDF 250 KB Available OnLine: 10. 08. 2011. Cited by