JSCS - Vol 73, No 7

JSCS Vol 73, No. 7

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J. Serb. Chem. Soc. 73 (7) 683–690 (2008)
UDC 544.526.5+542.92+547.56:546.3–386+546.215; JSCS–3751; doi: 10.2298/JSC0807683D; Original scientific paper

Characterization and biological evaluation of some novel pyrazolo[3’,4’:4,5]thieno[2,3-d]pyrimidin-8-ones synthesized via the Gewald reaction
DIPTI K. DODIYA, AMIT R. TRIVEDI, SAMIR H. JARSANIA, SHAILESH J. VAGHASIA and VIRESH H. SHAH
Department of Chemistry, Saurashtra University, Rajkot-360 005, Gujarat, India

(Received 6 December 2007, revised 13 March 2008)

The synthesis of substituted pyrazolo[3’,4’:4,5]thieno[2,3-d]pyrimidin-8-ones (IIIa–j) from 5-AMino-3-methyl-1H-thieno[3,2-c]pyrazole-6-carbonitrile (II) is described. The key compound II was synthesized from (5-methyl--2,4-dihydro-3H-pyrazol-3-ylidene)malononitrile I via the Gewald reaction. The synthesis of the title compounds IIIa–j was accomplished by condensation of II with different aromatic aldehydes. The newly synthesized heterocyles were characterized by elemental analysis, IR, ¹H-NMR, ¹³C-NMR and mass spectroscopic investigation. All the newly synthesized compounds were evaluated for antimicrobial activity against a variety of bacterial strains.

Keywords: pyrazolo[3’,4’:4,5]thieno[2,3-d]pyrimidin-8-ones; carbonitrile; Gewald reaction; antimicrobial activity.

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J. Serb. Chem. Soc. 73 (7) 691–701 (2008)
UDC 599.735.5+591.436+66–946.1:591.478–035.57; JSCS–3752; doi: 10.2298/JSC0807691N; Original scientific paper

Analysis of AMphetAMines illegally produced in Serbia
MARINA NEVESCANIN, SONJA BANOVIC STEVIC, SLOBODAN PETROVIC* and VLATKA VAJS**
Institute of Security, Kraljice Ane bb, 11 000 Belgrade, Serbia

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

**Faculty of Chemistry, University of Belgrade, Studentski Trg 16, 11001 Belgrade, Serbia

(Received 25 March 2008)

Forensic practice in the Republic of Serbia faced the illegal production of AMphetAMine for the first time in 2003. This paper presents the results of the chemical characterization of 32 batches of AMphetAMine sAMples from three separate cases, for the purpose of identification of the active components and additives. Through the profiling of impurities of all sAMples, using gas chromatography/mass spectrometry (GC/MS), 30 compounds associated with AMphetAMine were identified. The results of the analysis of powder tartrate, sulfate and phosphate salts of AMphetAMine, as well as variously formulated tablets are presented in this study. The analyses showed that the AMphetAMines were synthesized by the Leuckart method in all cases.

Keywords: AMphetAMine; impurity profiling; Leuckart synthesis.

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J. Serb. Chem. Soc. 73 (7) 703–711 (2008)
UDC 546.962+542.913:576+615.9; JSCS–3753; doi: 10.2298/JSC0807703L; Original scientific paper

Chemical composition and antimicrobial activity of the essential oil from Satureja horvatii Šilić (LAMiaceae)
BRANISLAVA LAKUSIC, MIHAILO RISTIC*, VIOLETA SLAVKOVSKA, JELENA ANTIC STANKOVIC** and MARINA MILENKOVIC**

Institute of Botany, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia

*Institute for Medicinal Plant Research “Josif Pancic“, Tadeusa Koscuskog 1, 11000 Belgrade, Serbia

**Institute of Microbiology, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia

(Received 16 October 2007, revised 18 January 2008)

The present paper describes the chemical composition and antimicrobial activity of the essential oil of the endemic species Satureja horvatii Šilić, collected in Montenegro. The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC–MS. From the 34 compounds representing 100 % of the oil, the major compound was the phenolic monoterpene thymol (63.37 %). The oil contained smaller AMounts of g-terpinene (7.49 %), carvacrol methyl ether (4.92 %), carvacrol (4.67 %), p-cymene (4.52%), a-terpinene (1.81 %), borneol (1.58 %), a-thujene (1.56 %), b-caryophyllene (1.55 %) and b-myrcene (1.44 %). The antimicrobial activity of the essential oil of S. horvatii was evaluated using the agar diffusion and broth microdilution methods. The essential oil exhibited antimicrobial activity to varying degrees against all the tested strains. The maximum activity of S. horvatii oil was observed against GrAM-positive bacteria (Micrococcus luteus, Staphylococcus epidermidis, Staphylococcus aureus and Enterococcus faecalis) and against the yeast (Candida albicans). The oil exhibited moderate activity against the GrAM-negative bacteria Escherichia coli and Klebsiella pneumoniae and weak activity against Pseudomonas aeruginosa. This study confirms that the essential oil of S. horvatii possesses antimicrobial activities in vitro against medically important pathogens.

Keywords: Satureja horvatii; endemic species; essential oil; GC–MS; antimicrobial activity.

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J. Serb. Chem. Soc. 73 (7) 713–726 (2008)
UDC 544.526.5+542.92+547.56:546.3–386+546.215; JSCS–3754; doi: 10.2298/JSC0807713B; Original scientific paper

Studies on Zn(II) monohydroxyphenyl mesoporphyrinic complexes. Synthesis and characterization
RICA BOSCENCU, RADU SOCOTEANU*, ANABELA S. OLIVEIRA** and LUIS FILIPE VIEIRA FERREIRA**
"Carol Davila" University of Medicine and Pharmacy, Faculty of Pharmacy, Inorganic Chemistry Department, Traian Vuia 6, Bucharest, Romania

*Romanian Academy, Institute of Physical Chemistry "I. G. Murgulescu", Splaiul Independentei 202, 77208 Bucharest, Romania

**Centro de Química-Física Molecular, Complexo Interdisciplinar, Instituto Superior Técnico, Universidade Técnica de Lisboa, Av. Rovisco Pais 1049-001, Lisbon, Portugal

(Received 27 July, revised 29 October 2007)

A series of four Zn(II) complexes with asymmetrical porphyrinic ligands were synthesized: [5-(4-hydroxyphenyl)-10,15,20-triphenyl-21H,23H-porphinato]Zn(II) (Zn(II)TPPOH_P), [5-(3-hydroxyphenyl)-10,15,20-triphenyl-21H,23H-porphinato]Zn(II) (Zn(II)TPPOH_M), [5-(2-hydroxyphenyl)-10,15,20-triphenyl-21H,23H-Zn(II)-porphinato]Zn(II) (Zn(II)TPPOH_O) and the well-known (5,10,15,20-tetraphenyl-21H,23H-porphinato]Zn(II) (Zn(II)TPP) as reference, in a 1:1 mole ratio. In all cases, the free-base porphyrin served as a tetradentate ligand through the four pyrrole nitrogen atoms. The complexes were characterized by elemental analysis, FTIR and UV–Vis spectroscopy, which fully confirmed the structure of the complexes. UV–Vis showed that the spectral absorption of the four complexes was blue-shifted by at least 50 nm compared to that of the free ligands. Also important structural data were obtained from several different NMR experiments (including ¹H-NMR, ¹³C-NMR, DEPT, COSY, HMBC and HMQC). Influences of external substituents on the porphyrin ring were observed.

Keywords: asymmetric porphyrins; Zn(II) porphyrin complexes; sensitizers for photodynAMic therapy; molecular absorption coefficients; NMR spectroscopy.

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J. Serb. Chem. Soc. 73 (7) 727–734 (2008)

UDC 544.032.4:66.094.1:546.92+544.478+546.26; JSCS–3755; doi: 10.2298/JSC0807727C; Original scientific paper

Ni(II), Pd(II) and Pt(II) complexes with ligand containing thiosemicarbazone and semicarbazone moiety: synthesis, characterization and biological investigation

SULEKH CHANDRA and MONIKA TYAGI

Department of Chemistry, Zakir Husain College, J. L. N. Marg, New Delhi – 110 002, India

(Received 28 November 2007, revised 2 April 2008)

The synthesis of nickel(II), palladium(II) and platinum(II) complexes with thiosemicarbazone and semicarbazone of p-tolualdehyde are reported. All the new compounds were characterized by elemental analysis, molar conductance measurements, magnetic susceptibility measurements, mass, ¹H-NMR, IR and electronic spectral studies. Based on the molar conductance measurements in DMSO, the complexes may be formulated as [Ni(L)₂Cl₂] and [M(L)₂]Cl₂ (where M = Pd(II) and Pt(II)) due to their non-electrolytic and 1:2 electrolytic nature, respectively. The spectral data are consistent with an octahedral geometry around Ni(II) and a square planar geometry for Pd(II) and Pt(II), in which the ligands act as bidentate chelating agents, coordinated through the nitrogen and sulphur/oxygen atoms. The ligands and their metal complexes were screened in vitro against fungal species Alternaria alternata, Aspergillus niger and Fusarium odum, using the food poison technique.

Keywords: thiosemicarbazone; semicarbazone; transition metal complexes; spectral studies; biological screening.

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J. Serb. Chem. Soc. 73 (7) 735–744 (2008)

UDC 543.551/.552+547–36:546.11'98+541.135.5; JSCS–3756; doi: 10.2298/JSC0807735B; Original scientific paper

Effect of excess free energy of solvents on the oxidation of methionine by quinolinium fluorochromate – A kinetic study

D. S. BHUVANESHWARI and K. P. ELANGO*

Department of Chemistry, PSNA College of Engineering and Technology, Dindigul – 624 622, TAMilnadu, India

*Department of Chemistry, GandhigrAM Rural University, GandhigrAM – 624 302, TAMilnadu, India

(Received 18 October 2007, revised 5 May 2008)

The oxidation of methionine by quinolinium fluorochromate (QFC) was studied in the presence of chloroacetic acid, in water/organic solvent mixtures of varying excess molar free energy function. The reaction is first order with respect to both QFC and acid. The reaction rates were determined at different temperatures and the activation parAMeters computed. The rate data was correlated with different solvent parAMeters using linear multiple regression analysis. From the results, information on the solvent–reactants and the solvent–transition state interactions was obtained.

Keywords: solvent effect; kinetics; methionine.

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J. Serb. Chem. Soc. 73 (7) 745–751 (2008)

UDC 62–405.8.004.12:544.6–188; JSCS–3757; doi: 10.2298/JSC0807745Е; Original scientific paper

Synthesis of biomorphic SiC and SiO₂ cerAMics

ADELA EGELJA, JELENA GULICOVSKI, ALEKSANDAR DEVECERSKI, BILJANA BABIC, MIROSLAV MILJKOVIC*, SNEZANA BOSKOVIC and BRANKO MATOVIC

Institute of Nuclear Sciences "Vinca", Belgrade, Serbia

*Center of Electron Microscopy, University of Nis, Serbia

(Received 23 October 2007, revised 21 April 2008)

Coniferous wood (fir) was transformed by pyrolysis into carbon preforms, which were subsequently converted into biomorphic cerAMics by the pressure infiltration technique with colloidal silica. An in situ reaction between the silica and the carbon template occurred in the cellular wall at a high sintering temperature. Depending on the employed atmosphere, non-oxide (SiC) or oxide (SiO₂) cerAMics were obtained. The morphology of the resulting porous cerAMics and their phase composition were investigated by scanning electron microscopy (SEM/EDX) and X-ray diffraction (XRD). The experimental results showed that the biomorphic cellular morphology of the wood maintained in both the SiC and silica cerAMics, which consisted of only the b-SiC phase and SiO₂, respectively.

Keywords: biomimetic synthesis; celular SiC; porous cerAMics.

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J. Serb. Chem. Soc. 73 (7) 753–760 (2008)

UDC 615.33:543.544.5:543–76; JSCS–3758; doi: 10.2298/JSC0807753N; Original scientific paper

The ionic equilibrium in the CuSO₄–H₂SO₄–H₂O system and the formation of the honeycomb-like structure during copper electrodeposition

NEBOJSA D. NIKOLIC*, LJUBICA J. PAVLOVIC*, GORAN BRANKOVIC**, MIOMIR G. PAVLOVIC* and KONSTANTIN I. POPOV*^,***

*ICTM – Department of Electrochemistry, University of Belgrade, Njegoseva 12, P.O. Box 473, 11001 Belgrade, Serbia

**Institute for Multidisciplinary Research, Kneza Viseslava 1a, 11030 Belgrade, Serbia

***Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3503, 11001 Belgrade, Serbia

(Received 26 September 2007, revised 26 March 2008)

The ionic equilibrium of the species in the CuSO₄–H₂SO₄–H₂O system was employed to systematize the conditions of copper electrodeposition leading to the formation of the honeycomb-like structure. The reason why CuSO₄ concentrations higher than 0.15 M are unsuitable for the formation of honeycomb-like structures is shown. The range of H₂SO₄ concentrations enabling the formation of this type of structure was also determined. The conditions leading to the formation of the honeycomb-like structures are: electrodeposition from solutions with lower concentrations of Cu(II) ions (0.15 M CuSO₄ and less) in a concentration range from 0.25 to 1.0 M H₂SO₄, at a temperature of 18.0±1.0 °C and at overpotentials outside the plateau of the limiting diffusion current density at which hydrogen evolution is vigorous enough to change the hydrodynAMic conditions in the near-electrode layer.

Keywords: electrolysis; hydrodynAMics; morphology; hydrogen; copper.

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J. Serb. Chem. Soc. 73 (7) 761–770 (2008)

UDC 553.492.004.54:504.53:58.051; JSCS–3759, doi: 10.2298/JSC0807761B; Original scientific paper

Molecular structure in correlation with electrochemical properties of mixed-ligand cobalt(III) complexes

K. BABIC-SAMARDZIJA, V. M. JOVANOVIC* and S. P. SOVILJ**

Rice University, Chemistry Department, 6100 Main St., Houston, TX 77005, USA,

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

**University of Belgrade, Faculty of Chemistry, P.O. Box 158, 11001 Belgrade, Serbia

(Received 9 October 2007, revised 3 March 2008)

Four mixed-ligand cobalt(III) complexes (1–4) of the general formula [Co(Rdtc)cyclAM](ClO₄)₂ and [Co(Rac)cyclAM](ClO₄)₂ (cyclAM = 1,4,8,11-tetraazacyclotetradecane; Rdtc = thiomorpholine-(Timdtc) or 2-methylpiperidine-(2-Mepipdtc) dithiocarbAMates; Rac = 1,1,1,5,5,5-hexafluoro-2,4-pentanedionato (Hfac) or 2,2,6,6-tetrAMethyl-3,5-heptanedionato (Tmhd), respectively) were electrochemically exAMined on a glassy carbon and an iron electrode in perchloric acid solution. The obtained results showed the influence of these complexes on hydrogen evolution, the oxygen reduction reaction and iron dissolution. The exhibited effects of the complexes on these reactions depend on structure related to the bidentate dithiocarbAMato or b-diketonato ligand. The electrochemical properties of the complexes were correlated with molecular structure and parAMeters derived from spectral analysis and molecular modeling.

Keywords: cobalt(III) complexes; cyclAM; dithiocarbAMato ligands; b-diketonato ligands; MOT.

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