JSCS - Vol 73, No 10

JSCS Vol 73, No. 10

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J. Serb. Chem. Soc. 73 (10) 937–943 (2008)
UDC 547–304.4+546.33–36:615.281/.282; JSCS–3774; doi: 10.2298/JSC0810937K; Original scientific paper

Synthesis and antimicrobial, antifungal and anthelmintic activities of 3H-1,5-benzodiazepine derivatives
RAJESH KUMAR and Y. C. JOSHI
Department of Chemistry, University of Rajasthan, Jaipur, India

(Received 1 August 2007, revised 14 January 2008)

The diazonium salt of 4-AMino-1-methyl-3-propyl-1H-pyrazole-5-carboxAMide in the presence of sodium hydroxide was condensed with different β-diketones/β-ketoesters, 3a–e, to obtain new β-diketones/β-ketoesters, 4a–e. The β-diketones/β-ketoesters 4a–e were condensed with o-phenylenediAMine (o-PDA) in presence of p-toluenesulfonic acid/SiO₂ to give biologically active 3H-1,5-benzodiazepines, 5a–e. All the newly synthesized compounds were characterized by elemental analysis and spectral studies. The compounds 5a–e was screened for their antimicrobial, antifungal and anthelmintic activities.

Keywords: 1,5-benzodiazepines; β-diketones/β-ketoesters; substituted pyrazole; p-toluenesulfonic acid.

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J. Serb. Chem. Soc. 73 (10) 945–950 (2008)
UDC 547–327+66.095.253:54–732+537.5:544.015.4; JSCS–3775; doi: 10.2298/JSC0810945M; Short communication

SHORT COMMUNICATION

Benzylation of N-phenyl-2-phenylacetAMide under microwave irradiation
DUSAN Z. MIJIN*, MASA PRASCEVIC* and SLOBODAN D. PETROVIC*^,**
*Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3503, 11120 Belgrade, Serbia

**Hemofarm, Beogradski put b.b., 26300 Vrsac, Serbia

(Received 5 July, revised 21 November 2007)

N-Phenyl-2-phenylacetAMide was alkylated with benzyl chloride in the presence of powdered potassium hydroxide under microwave irradiation in a solvent-free system. The reactions were also performed in the presence of phase-transfer catalysts. The formation of N-, O- and C-products of alkylation was followed by gas chromatography. The N-product was found to be the main product under microwave irradiation. The O-product was obtained in higher yields when an excess of base and benzyl chloride was used.

Keywords: alkylation; AMides; phenylacetAMides; phase-transfer conditions; microwave irradiation.

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J. Serb. Chem. Soc. 73 (10) 951–959 (2008)
UDC 632.95+504.53:577.152.1:57.018.8+546.26; JSCS–3776; doi: 10.2298/JSC0810951R; Original scientific paper

The impact of atrazine on several biochemical properties of chernozem soil
LJ. RADIVOJEVIC, S. GASIC, LJ. SANTRIC and R. STANKOVIC-KALEZIC

Institute of Pesticides and Environmental Protection, Banatska 31b, P.O. Box 163, 11080 Belgrade, Serbia

(Received 18 January, revised 11 May 2008)

The impact of the pesticide atrazine on biochemical processes in soil was investigated. Atrazine loadings of 8.0, 40.0 and 80.0 mg/kg soil were laboratory tested in an experiment set up on a clay loAM soil. Dehydrogenase activity, change in biomass carbon, soil respiration and metabolic coefficient were exAMined. The sAMples were collected for analysis 1, 7, 14, 21, 30 and 60 days after atrazine application. The acquired data indicated that the effect of atrazine on the biochemical activity of the soil depended on its application rate and duration of activity, and the effect was either stimulating or inhibiting. However, the detected changes were found to be transient, indicating that there is no real risk of the compound disrupting the balance of biochemical processes in soil.

Keywords: atrazine; soil; dehydrogenase; biomass carbon; respiration.

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J. Serb. Chem. Soc. 73 (10) 961–965 (2008)
UDC *Nepeta rtanjensis:665.52/.54:615.282–188; JSCS–3777; doi: 10.2298/JSC0810961L; Short communication

SHORT COMMUNICATION

Antifungal activity of Nepeta rtanjensis essential oil
MILICA LJALJEVIC GRBIC, MILOS STUPAR, JELENA VUKOJEVIC, MARINA SOKOVIC*, DANIJELA MISIC*, DRAGOLJUB GRUBISIC* and MIHAILO RISTIC**
Institute of Botany and Botanical Garden “Jevremovac”, Faculty of Biology, University of Belgrade, Takovska 43, 11000 Belgrade, Serbia

*Institute for Biological Research “Sinisa Stankovic”, Bulevar Despota Stefana 142, 11000 Belgrade, Serbia

**Institute of Medicinal Plant Research “Dr. Josif Pancic”, Tadeusa Koscuska 1, 11000 Belgrade, Serbia

(Received 14 April, revised 27 May 2008)

The chemical composition and antifungal activity of the essential oil of an endemic Serbian plant Nepeta rtanjensis Diklić &AMp; Milojević was studied. The essential oil was isolated from cultivated plants. Inhibition of mycelia growth of five micromycetes, two Alternaria species originally isolated from N. rtanjensis, Cladosporium cladosporoides, Trichoderma viride and Bipolaris spicifera, were tested using the agar dilution method. The essential oil of N. rtanjensis, the main component of which was 4aα,7α,7αβ-nepetalactone, showed strong antifungal activity against all the tested micromycetes. The minimum inhibitory concentration of N. rtanjensis essential oil ranged from 0.6 to 1.4 μg mL^-1. The fungi most sensitive to the tested oil were Alternaria species, while Trichoderma viride was the most resistant.

Keywords: Nepeta rtanjensis; essential oil; antifungal activity.

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J. Serb. Chem. Soc. 73 (10) 967–978 (2008)

UDC 577.15:547.53:615.281–188; JSCS–3778; doi: 10.2298/JSC0810967P; Original scientific paper

The effect of lipophilicity on the antibacterial activity of some 1-benzylbenzimidazole derivatives

S. O. PODUNAVAC-KUZMANOVIC, D. D. CVETKOVIC and D. J. BARNA*

Faculty of Technology, Bulevar Cara Lazara 1, 21000 Novi Sad, Serbia

*Institute of Public Health, Zmaj Jovina 30, 24000 Subotica, Serbia

(Received 27 February, revised 13 May 2008)

In the present paper, the antibacterial activity of some 1-benzylbenzimidazole derivatives were evaluated against the GrAM-negative bacteria Escherichia coli. The minimum inhibitory concentration was determined for all the compounds. Quantitative structure–activity relationship (QSAR) was employed to study the effect of the lipophilicity parAMeters (log P) on the inhibitory activity. Log P values for the target compounds were experimentally determined by the “shake-flask” method and calculated by using eight different software products. Multiple linear regression was used to correlate the log P values and antibacterial activity of the studied benzimidazole derivatives. The results are discussed based on statistical data. The most acceptable QSAR models for the prediction of the antibacterial activity of the investigated series of benzimidazoles were developed. High agreement between the experimental and predicted inhibitory values was obtained. The results of this study indicate that the lipophilicity parAMeter has a significant effect on the antibacterial activity of this class of compounds, which simplifies the design of new biologically active molecules.

Keywords: benzimidazole derivatives; lipophilicity; quantitative structure–activity relationship; antibacterial; in vitro studies.

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J. Serb. Chem. Soc. 73 (10) 979–988 (2008)

UDC 546.34+537.622.4:542.913:547.476.1; JSCS–3779; doi: 10.2298/JSC0810979G; Original scientific paper

Synthesis of lithium ferrites from polymetallic carboxylates

DANA GINGASU, IOANA MINDRU, LUMINITA PATRON and STEFANIA STOLERIU*

“Ilie Murgulescu” Institute of Physical Chemistry, Spl. Independentei 202, Bucharest 060021, Romania

*“Politehnica” University of Bucharest, Faculty of Chemistry, Department SIMO, Polizu Street 1–7, Bucharest, Romania

(Received 6 March, revised 20 May 2008)

Lithium ferrite was prepared by the thermal decomposition of three polynuclear complex compounds containing as ligands the anions of malic, tartaric and gluconic acid: (NH₄)₂[Fe_2.5Li_0.5(C₄H₄O₅)₃(OH)₄(H₂O)₂]×4H2O (I), (NH₄)₆[Fe_2.5Li_0.5(C₄H₄O₆)₃(OH)₈]×2H₂O (II) and (NH₄)₂[Fe_2.5Li_0.5(C₆H₁₁O₇)₃(OH)₇] (III). The polynuclear complex precursors were characterized by chemical analysis, IR and UV–Vis spectra, magnetic measurements and thermal analysis. The obtained lithium ferrites were characterized by XRD, scanning electron microscopy, IR spectra and magnetic measurements. The single α-Li_0.5Fe_2.5O₄ phase was obtained by thermal decomposition of the tartarate complex annealed at 700 °C for 1 h. The magnetization value ≈ 50 emu g^-1 is lower than that obtained for the bulk lithium ferrite due to the nanostructural character of the ferrite. The particle size was smaller than 100 nm.

Keywords: lithium ferrite; chemical synthesis; thermogravimetric analysis (TGA); X-ray diffraction; magnetic properties.

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J. Serb. Chem. Soc. 73 (10) 989–995 (2008)

UDC 537.872+539.124:547.686:54.022+541.5; JSCS–3780; doi: 10.2298/JSC0810989D; Original scientific paper

The Hall rule in fluoranthene-type benzenoid hydrocarbons

JELENA DJURDJEVIC, SLAVKO RADENKOVIC and IVAN GUTMAN

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

(Received 20 May 2008)

The applicability of the Hall rule (linear relation between the total π-electron energy and the number of Kekulé structures) was investigated in the case of fluoranthene-type benzenoid hydrocarbons. It was found that the original Hall rule is not obeyed, but holds for sets of isomers with a fixed number of bay regions. For such groups of isomers, two apparently contradictory Hall-type rules were conceived, and it was found that both give almost identical numerical results.

Keywords: Hall rule; total π-electron energy; Kekulé structures; fluoranthene; benzenoid hydrocarbons; fluoranthene-type hydrocarbons.

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J. Serb. Chem. Soc. 73 (6) 997–1009 (2008)

UDC 546.47–31:544.478:66.094.258+547.264; JSCS–3781; doi: 10.2298/JSC0810997S; Original scientific paper

Characterization of various zinc oxide catalysts and their activity in the dehydration–dehydrogenation of isobutanol

LAMIA SAAD and MARY RIAD

Refining Division – Egyptian Petroleum Research Institute, Nasr City, Hai Al-Zehour, P. O. Box 11727, Cairo, Egypt

(Received 24 Novembar 2007, revised 23 January 2008)

Mono and bifunctional zinc oxide catalysts were prepared to study their activity in the catalytic conversion of isobutanol. The prepared catalysts were characterized by X-ray diffraction analysis and nitrogen adsorption measurements. The conversion of isobutanol was taken as a model reaction to measure the catalytic activity of the prepared oxide catalysts. The overall conversion yield of competitive dehydration–dehydrogenation reactions of isobutanol was found to be higher over the binary oxide catalysts than over the single oxide one at all reaction temperature within the range 250–400 °C. The binary oxide catalysts were more selective for isobutene, as the predominant dehydrated product. The single oxide catalyst exhibited higher selectivity towards isobutyraldehyde as the dehydrogenated product, and the selectivity increased with increasing reaction temperature.

Keywords: metal oxides; acid–base catalysis; isobutanol conversion.

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J. Serb. Chem. Soc. 73 (10) 1011–1019(2008)

UDC 667.287.4:536.75+536.722:543.24; JSCS–3782, doi: 10.2298/JSC0810011G; Original scientific paper

ThermodynAMic characterization of the dimerization equilibrium of newly synthesized polymethine cyanine dyes

JAHAN B. GHASEMI, FERESHTEH SHIRI, TODOR G. DELIGEORGIEV* and MIKAEL KUBISTA**

Chemistry Department, Faculty of Sciences, Razi University, Kermanshah, Iran

*Faculty of Chemistry, University of Sofia, 1164 Sofia, Bulgaria

**TATAA Biocenter AB, Sahlgrenska Science Park, Medicinaregatan 8A, Göteborg, Sweden

(Received 14 September 2007, revised 16 June 2008)

The monomer–dimer equilibrium and thermodynAMics of three new cyanine dyes were investigated by spectrophotometric and chemometric methods. The dimerization constants of these new cyanine dyes were determined by studying the dependence of their absorption spectra on the temperature in the range 25–80 °C at concentrations of 3.0×10-4, 1.9×10-4 and 1.1×10-4 M for dye 1, 2 and 3, respectively. The processing of the data, performed for the quantitative analysis of pure spectral profiles, was based on the simultaneous resolution of the overlapping bands in the whole set of absorption spectra. From the dimerization constant and its dependence on temperature, the values of the standard enthalpy change and entropy change of dimerization were calculated.

Keywords: chemometrics; dimerization; cyanine dyes; absorption titration; enthalpy; entropy.

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