JSCS Vol 77, No. 5

Publication of this issue is financially co-supported by LUKOIL Srbija AD

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J. Serb. Chem. Soc. 77 (5) 569–579 (2012)

UDC 547.826.2+544.353.2+544.351–145.82+547.631+547.235; JSCS–4290; doi: 10.2298/JSC120223019D; Original scientific paper

 

Effects of solvent and structure on the reactivity of 2-substituted nicotinic acids with diazodiphenylmethane in aprotic solvents

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

Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11121 Belgrade, Serbia

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

 

(Received 23 February, revised 5 March 2012)

The rate constants for the reactions of diazodiphenylmethane (DDM) with 2-substituted nicotinic acids in nine aprotic solvents at 30 °C were determined. The obtained second order rate constants in aprotic solvents were correlated using the KAMlet–Taft solvatochromic equation in the complete form: log k = log k0 + sp + aa + bb. The correlations of the kinetic data were realized by means of multiple linear regression analysis. The obtained results were analyzed in terms of the initial and the transition state of the reaction and compared with previously determined kinetic data for nicotinic acid. The signs of the equation coefficients (s, a and b) are in agreement with the reaction mechanism and the influence of the solvent on the reaction rate is discussed based on the correlation results. The mode of the transmission of the substituent effect is discussed in light of the contribution of solute–solvent interaction to the reactivity of the acid. The substituent effect was additionally analyzed by the HAMmett equation, log k = rs + log k0.

 

Keywords: pyridinecarboxylic acids; diazodiphenylmethane; reaction rate constants; solvatochromic parAMeters; aprotic solvents.

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J. Serb. Chem. Soc. 77 (5) 581–588 (2012)

UDC 544.412.1:547.56+547.53–304.9:547.53.024+547.264; JSCS–4291; doi: 10.2298/JSC110526202L; Short communication

 

Preparation of 2-heteroatom substituted-4-oxo-4-arylbutanoates via thio- and aza-Michael addition

HUILI LIU, XIN LV, LIEJIN ZHOU, RUIFENG YIN and XIAOXIA WANG

Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, P. R. China

 

(Received 25 July, revised 11 November 2011)

Efficient regioselective conjugate additions of thiophenols and benzotriazole to 4-aryl-4-oxobut-2-enoates were achieved under mild conditions. Thus, a variety of 2-(arylthio)-4-oxo-4-arylbutanoates and 2-benzotriazolyl-4-oxo--4-arylbutanoates were conveniently synthesized in good to excellent yields.

 

Keywords: Michael addition; thiophenol; benzotriazole; 4-aryl-4-oxobut-2-enoate

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J. Serb. Chem. Soc. 77 (5) 589–597 (2012)

UDC 547.588.18+547.233+547–316+547.281.1:615.28:615.277; JSCS–4292; doi: 10.2298/JSC110310170M; Original scientific paper

 

Synthesis and evaluation of some novel derivatives of 2-propoxybenzylideneisonicotinohydrazide for their potential antimicrobial activity

MANAV MALHOTRA, MANU ARORA*, ABDUL SAMAD**, KAPENDRA SAHU***, PRIYANKA PHOGAT**** and AAKASH DEEP*****

Department of Pharmaceutical Chemistry, Meerut Institute of Engineering and Technology, Bypass Road-Baghpat Crossing, Meerut-250005, Uttar Pradesh, India

*Institute of Pharmacy and Emerging Sciences, Baddi University, Baddi-173205, India

**Department of Pharmaceutical Chemistry, College of Pharmacy in Al-Kharj, King Saud University, Riyadh, Saudi Arabia

***Department of Pharmaceutical Sciences, Rajiv Gandhi Technical University, Bhopal-462033, India
****Department of Pharmaceutical Sciences, Hindu College of Pharmacy, Sonepat-131001, India

*****Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak-124001, India

 

(Received 10 March, revised 18 June 2011)

A novel series of Mannich bases containing isoniazid were prepared. First, reaction of 2-propoxybenzaldehyde with isoniazid gave the corresponding hydrazone (2a). Subsequently, product 2a after the Mannich reaction of AMinomethylation with formaldehyde and secondary AMines gave 2b–k. The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against the A549 human lung adenocarcinoma cell line. Compounds 2c and 2k displayed moderate to potent antimicrobial activity against all the tested strains and they also exhibited significant cytotoxicity in a dose-dependent manner with IC50 values ranging from 2.84 to 8.55 µg/mL and 0.007–0.030 mM. The structures of the newly synthesized compounds were evaluated by elemental and spectral (IR, 1H-NMR, 13C-NMR) methods. The results demonstrated the potential and importance of developing new Mannich bases which would be effective against resistant microbial strains and may be useful leads for anticancer drug development in the future.

 

Keywords: benzylidene; antimicrobial; cytotoxicity; Mannich bases; 1H-NMR; 13C-NMR.

Full Article - PDF PDF 184 KB               Supplementary Material PDF PDF 135 KB          Available OnLine: 18. 11. 2011.        Cited by

J. Serb. Chem. Soc. 77 (5) 599–605 (2012)

UDC 547.433–304.2+547.789.1+542.913:57–188; JSCS–4293; doi: 10.2298/JSC110616002S; Original scientific paper

 

Synthesis of 2-oxoazetidine derivatives of 2-AMinothiazole and their biological activity

PUSHKAL SAMADHIYA, RITU SHARMA, SANTOSH K. SRIVASTAVA and SAVITRI D. SRIVASTAVA

Synthesis Organic Chemistry Laboratory, Department of Chemistry, Dr. H.S. Gour University, Sagar, Madhya Pradesh-470003, India

 

(Received 5 January, revised 16 June 2011)

A new series of 3-chloro-4-(substituted phenyl)-1-{[2-(2-thiazolylAMino)ethyl]AMino}-2-azetidinone, compounds 4a–m, has been synthesized from 2-AMinothiazole as the starting material. The structures of all the synthesized compounds were confirmed by chemical and spectral analyses, such as FTIR, 1H-NMR and 13C-NMR spectroscopy. All the final synthesized compounds 4a–m were screened for their antibacterial and antifungal activities against some selected bacteria and fungi and for their antitubercular activity against Mycobacterium tuberculosis, and their minimum inhibitory concentration (MIC) values were determined. The anti-inflAMmatory activities of the title compounds were screened using albino rats (either sex) and gave acceptable results.

 

Keywords: synthesis; 2-AMinothiazole; azetidinone; antimicrobial; antitubercular; anti-inflAMmatory.

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J. Serb. Chem. Soc. 77 (5) 607–617 (2012)

UDC 577.175.72+57.088+57.017.6/.7:577.112; JSCS–4294; doi: 10.2298/JSC110831211M; Original scientific paper

 

Isolation of complexes formed between insulin-like growth factor-binding protein-3 and transferrin from human serum

GORAN MILJUŠ, MIOMIR PETROVIĆ and OLGICA NEDIĆ

Institute for the Application of Nuclear Energy – INEP, University of Belgrade, Banatska 31b, 11080 Belgrade – Zemun, Serbia

 

(Received 31 August, revised 7 December 2011)

Insulin-like growth factors (IGFs) play an important role in the regulation of cell growth, differentiation and metabolism. The AMount of free, biologically active IGFs is regulated by the IGF-binding proteins (IGFBPs). IGFBP-3 is the most abundant binding protein and it is known to interact with other circulating proteins, including transferrin (Tf). In order to elucidate the possible role of IGF/IGFBP-3 in the metabolism of iron, it is necessary to isolate IGFBP-3/Tf complexes. Several affinity-based techniques were employed. The results showed that only the double immunoprecipitation method with anti-Tf and anti-IGFBP-3 antibodies selectively separated the complexes from other molecular forms, such as monomers, oligomers or fragments of IGFBP-3 and Tf. The isolated complexes can now be used to investigate the relationship between IGF/IGFBP-3 and iron, both in structural and metabolic terms.

 

Keywords: IGFBP-3; transferrin; complex; isolation.

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J. Serb. Chem. Soc. 77 (5) 619–626 (2012)

UDC *Galatella linosyris:665.52/.54:615.28–188; JSCS–4295; doi: 10.2298/JSC110915213G; Original scientific paper

 

Composition and antimicrobial activity of the essential oil from Galatella linosyris (L.) Rchb. f. (Asteraceae)

DEJAN GOĐEVAC, LJUBODRAG VUJISIĆ*, IVAN VUČKOVIĆ*, VLATKA VAJS, MARINA SOKOVIĆ**, PETAR D. MARIN*** AND VELE TEŠEVIĆ*

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

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158, 11000 Belgrade, Serbia

**Institute for Biological Research “Siniša Stanković”, University of Belgrade, Bulevar despota Stefana 142, 11000 Belgrade, Serbia

***Faculty of Biology, University of Belgrade, Institute of Botany and Botanical Garden “Jevremovac”, Studentski trg 16, 11000 Belgrade, Serbia

 

(Received 15 September, revised 15 December 2011)

An investigation of the chemical composition and antimicrobial activity of the essential oil of Galatella linosyris is presented. The chemical analysis (GC/MS, NMR) showed that sabinene (40 %), β-pinene (35.5 %), α-pinene (4.5 %), limonene (4 %), γ-muurolene (4 %), and (E)-caryophyllene (3.3 %) were dominant components in this oil. Microdilution assays were used to evaluate the minimum inhibitory concentration (MIC) and the minimum bactericidal/fungicidal concentrations (MBC/MFC). G. linosyris essential oil exhibited better antibacterial activity against some of the tested bacteria than antifungal activity.

 

Keywords: Galatella linosyris; essential oil; antimicrobial activity; GC/MS; NMR.

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J. Serb. Chem. Soc. 77 (5) 627–637 (2012)

UDC 546.562’732’742:547+57–188:615.281/.282; JSCS–4296; doi: 10.2298/JSC110412148S Original scientific paper

 

Physico-chemical and biological studies of Cu(II), Co(II) and Ni(II) complexes of an N4 coordinating ligand derived from the Schiff base of diacetyl with ethylenediAMine and benzoic acid

NETRA PAL SINGH and ABHAY NANDA SRIVASTAVA

Department of Chemistry, Meerut College, Meerut-250001, India

 

(Received 12 April, revised 28 August 2011)

Mononuclear metal complexes of the type [ML1]Cl2 (where, M = Cu(II), Co(II) or Ni(II) and L1 = ligand) were synthesized by the reaction of a new N4 coordinating ligand, N,N’-{(1,2-dimethylethanediylidene)bis[nitrilo(2,1-ethanediyl)]}bis[benzAMide] derived from the Schiff base of diacetyl with ethylenediAMine and benzoic acid, and the corresponding hydrated metal chloride salts. The metal complexes were characterized by elemental analysis, melting point determination, molar conductance and magnetic moment measurements, IR, UV–Vis, 1H- and 13C-NMR, and ESR spectroscopy. The ligand and all the metal complexes were stable in the solid state at room temperature. From the analytical and spectroscopic investigations, the stoichiometry of the complexes was found to be 1:1 (metal:ligand). Based on the electronic spectra and magnetic moment data, the metal complexes had a square planar geometry. The molar conductance values show the 1:2 electrolytic nature of the metal complexes. A cyclic voltAMmetric study of the Cu(II) metal complex has also performed, which showed one electron quasi-reversible reduction around –0.92 to –1.10 V. In vitro biological activities of the ligand and metal complexes was checked against two bacteria Bacillus subtilis and Escherichia coli and two fungi Aspirgillus niger and A. flavus which showed the antibacterial and antifungal properties of the ligand and its metal complexes.

 

Keywords: mononuclear Cu(II), Co(II) and Ni(II) complexes; square planar geometry; antibacterial and antifungal properties.

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J. Serb. Chem. Soc. 77 (5) 639–650 (2012)

UDC 547.354:544.132:544.723.232:519.254:519.233.5; JSCS–4297; doi: 10.2298/JSC110804205A Original scientific paper

 

A quantitative structure–activity relationship study on histAMine receptor antagonists using the genetic algorithm–multi-parAMeter linear regression method

MARYAM ADIMI, MAHMOUD SALIMI*, MEHDI NEKOEI**, ESLAM POURBASHEER*** AND ABOLGHASEM BEHESHTI***

Chemical Engineering Department, Faculty of Engineering, IslAMic Azad University – Farahan Branch, Farmahin, Iran

*Chemical Engineering Department , Faculty of Engineering, IslAMic Azad University – Arak Branch, Arak, Iran

**Department of Chemistry, Shahrood branch, IslAMic Azad University, Shahrood, Iran

***Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, P. O. Box 14155-6455, Tehran, Iran

 

(Received 4 August 2011)

A quantitative structure activity relationship (QSAR) model has been generated for predicting the antagonist potency of biphenyl derivatives as human histAMine (H3) receptors. The molecular structures of the compounds were numerically represented by various kinds of molecular descriptors. The whole data set was divided into training and test sets. A genetic algorithm based multiple linear regression was used to select the most statistically effective descriptors. The final QSAR model (N = 24, R2=0.916, F = 51.771, Q2LOO = 0.872, Q2LGO = 0.847, Q2BOOT = 0.857) was fully validated employing the leave-one-out (LOO) cross-validation approach, Fischer statistics (F), the Y-randomization test, and predictions based on the test data set. The test set presented an external prediction power of R2test = 0.855. In conclusion, the generated QSAR model could be used as a valuable tool for designing similar groups of new antagonists of histAMine (H3) receptors.

 

Keywords: QSAR; genetic algorithm; multiple linear regression; biphenyl derivatives; histAMine (H3) receptors.

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J. Serb. Chem. Soc. 77 (5) 651–665 (2012)

UDC 669–492.2/.3–.034.3+544.6.018.4:532.14; JSCS–4298; doi: 10.2298/JSC110627196O Original scientific paper

 

Effect of electrolysis parAMeters on the morphologies of copper powders obtained at high current densities

GÖKHAN ORHAN and GIZEM GÜZEY GEZGIN

Istanbul University, Faculty of Engineering, Metallurgical and Materials Engineering Department, 34320 Istanbul, Turkey

 

(Received 27 June, revised 20 October 2011)

The effects of copper ion concentrations and electrolyte temperature on the morphologies and on the apparent densities of electrolytic copper powders deposited at high current densities under galvanostatic control were exAMined. These parAMeters were evaluated by the current efficiency of hydrogen evolution. In addition, scanning electron microscopy was employed for analyzing the morphology of the copper powders. It was found that the morphology was dependent on the copper ion concentration and electrolyte temperature under sAMe current density (CD) conditions. At 150 mA cm-2 and a potential of 1000±20 mV (vs. SCE), porous and disperse copper powders were obtained at low concentrations of Cu ions (0.120 M Cu2+ in 0.50 M H2SO4). Under these conditions, a high rate of hydrogen evolution occurred parallel to copper electrodeposition. The morphology was changed from porous, disperse and cauliflower-like to coral-like, shrub-like and stalk–stock-like morphology with increasing Cu ion concentrations from 0.120, through 0.155, 0.315 and 0.475 to 0.630 M Cu2+ in 0.5 M H2SO4, respectively, at the sAMe CD. Similarly, with increasing temperature, the powder morphology and the apparent density changed. The apparent density values of the copper powders were suitable for many powder metallurgy applications.

 

Keywords: electrolytic copper powder; apparent density; hydrogen evolution; scanning electron microscopy (SEM).

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J. Serb. Chem. Soc. 77 (5) 667–683 (2012)

UDC 546.16–123+547.587.4+547.56+547.466:543.544; JSCS–4299; doi: 10.2298/JSC110304003P; Original scientific paper

 

Different behaviour of 3-nitrotyrosine and tyrosine toward perfluorinated reagents suitable for the one-step preparation of volatile derivatives

RADMILA PAVLOVIĆ*,**, PIER ANTONIO BIONDI***, LUCA MARIA CHIESA***, NATAŠA TRUTIĆ**, MIRJANA ABRAMOVIĆ** AND ENZO SANTANIELLO*

*Department of Medicine, Surgery and Dentistry, School of Medicine c/o S. Paolo Hospital, Università degli Studi di Milano, Italy

**Department of Chemistry, Medical Faculty, University of Niš, Serbia

***Department of Veterinary Sciences and Technologies for Food Safety, Faculty of Veterinary Medicine, Università degli Studi di Milano, Italy

(Received 4 March 2011, revised 10 January 2012)

 

With the view of developing a gas-chromatographic (GC) determination of the 3-nitrotyrosine (NY)/tyrosine (Y) ratio as a marker of nitro-oxidative stress, different reagents were tested with the objective of obtaining a single volatile fluorinated product for each AMino acid in a one-step derivatisation procedure. The heptafluorobutyric anhydride (HFBA)/heptafluorobutanol (HFBOH) mixture proved unsuccessful for the simultaneous analysis of NY and Y. The reaction with different chloroformates, isobutyl chlorofomate (iBuCF) and ethyl chloroformate (EtCF) in the presence of different perfluorinated alcohols, such as trifluoroethanol (TFEOH) and HFBOH, was investigated. A combination EtCF/fluorinated alcohols yielded derivatives of NY and Y as single peaks suitable for the GC determination of the NY/Y ratio. The different behaviours of the two AMino acids in the employed reaction mixtures and the parAMeters influencing the results are discussed.

 

Keywords: perfluorinated derivatives; tyrosine; 3-nitrotyrosine; GC–MS.

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J. Serb. Chem. Soc. 77 (5) 685–697 (2012)

UDC 678.744.32’327+546.766+546.13:66.095.2.094.3; JSCS–4300; doi: 10.2298/JSC110131216T; Original scientific paper

 

Modified polyacrylAMide-supported chlorochromate as a new polymeric oxidizing agent

BAHMAN TAMAMI, ROGHAYEH HEIRAN and ELHAM RIAZI MONTAZER

Department of Chemistry, Shiraz University, Shiraz-71454, Iran

 

(Received 31 January, revised 21 December 2011)

Modified polyacrylAMide-supported chlorochromate was synthesized and used as a versatile and efficient oxidizing agent for the oxidation of various organic compounds, such as hydroxyl compounds, silylethers, oximes, thiols, and others. Over oxidation of the products (aldehydes to carboxylic acids) was not observed with this oxidizing agent. The oxidant was insoluble in the oxidation media and the chromium(VI) ions remained firmly bound to the insoluble polymeric support after the oxidation reaction. The mild reaction condition, easy work-up, short reaction times, regenerability of the reagent and its easy preparation and handling are AMong the advantages of this new polymeric chlorochromate reagent.

 

Keywords: chromium(VI) oxidant; modified polyacrylAMide; polymeric oxidizing agent; chlorochromate.

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J. Serb. Chem. Soc. 77 (5) 699–714 (2012)

UDC 66.017:620.1+546.82–31:536.5.004.12:543.57; JSCS–4301; doi: 10.2298/JSC110331161R; Original scientific paper

 

The influence of shaped TiO2 nanofillers on the thermal properties of poly(vinyl alcohol)

MARIJA B. RADOIČIĆ, ZORAN V. ŠAPONJIĆ, MILENA T. MARINOVIĆ-CINCOVIĆ, SCOTT P. AHRENKIEL*, NATAŠA M. BIBIĆ and JOVAN M. NEDELJKOVIĆ

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

*South Dakota School of Mines and Technology, Rapid City, SD, USA

 

(Received 31 March, revised 29 June 2011)

Poly(vinyl alcohol)-based nanocomposites consisting of shaped TiO2 nanocrystals (nanoparticles, nanotubes or nanorods) were synthesized by direct blending of the polymer and a solution of titania nanocrystals or powder. In order to elucidate the influence of the shape of the titania nanocrystals on thermal stability of the polymer matrix and particles interaction with poly(vinyl alcohol) (PVA) chains, structural and thermal characterizations of PVA/TiO2 nanocomposites were performed. Faceted nanoparticles increased the thermal stability of the PVA matrix. Titania nanotubes and nanorods did not show any stabilizing effect on the polymer matrix under an argon atmosphere. The thermo-oxidative degradation temperature of PVA increased with addition of faceted TiO2 nanoparticles. The thermo-oxidative stability of the PVA matrix was affected more by the presence of titania nanotubes and nanorods in comparison with its thermal stability under an inert atmosphere. The degree crystallinity (Xc=32 %) of the PVA matrix slightly decreased in the presence of the faceted TiO2 nanoparticles in nanocomposite sAMples.

 

Keywords: nanocomposite materials; thermal properties; differential scanning calorimetry; thermogravimetric analysis; TiO2; poly(vinyl alcohol).

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J. Serb. Chem. Soc. 77 (5) 715 (2012)

 

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