JSCS
Vol 76, No. 2
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J. Serb. Chem. Soc. 76 (2) 155–163 (2011)
UDC
66.095.11+547.857.8:678.746:547–316; JSCS–4108; doi: 10.2298/JSC100215010P; Original scientific paper
Friedel–Crafts
acylation of arenes with carboxylic acids using polystyrene-supported aluminum
triflate
KAVEH PARVANAK BOROUJENI and KAMRAN PARVANAK*
Department
of Chemistry, Shahrekord University, Shahrekord 115, Iran
*IslAMic
Azad University, Shahr-e-Rey Branch, Iran
(Received 15 February, revised 1
September 2010)
Cross-linked polystyrene-supported aluminum triflate
(Ps–Al(OTf)3) has been shown to be a mild,
efficient, and chemoselective heterogeneous Lewis acid catalyst for the
acylation of aromatic compounds. The catalyst can be easily prepared from cheap
starting materials, is stable (as
a bench top catalyst) and is
reusable.
Keywords: acylation; ketones; aluminum triflate; polystyrene.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2) 165–175 (2011)
UDC
542.913+547.367+547.79:615.281/.282; JSCS–4109; doi: 10.2298/JSC090421001D; Original scientific paper
Synthesis of selected 5-thio-substituted tetrazole derivatives and
evaluation of their antibacterial and antifungal activities
VARADARAJI DHAYANITHI, SUBAN SHAFI SYED, KUBARAN
KUMARAN, KASI REGURAMAN JAI SANKAR, RAMASWAMY
VENKAT RAGAVAN*, PALUSA SANATH KUMAR GOUD**, NALILU SUCHETHA KUMARI*** and HARI NARAYAN PATI****
P.G. and Research Department of Chemistry, IslAMiah
College, VaniyAMbadi 632 752, India
*Chemistry
Division, School of Science and Humanities, VIT University, Vellore 632 014,
Indi
**N.
E. T. College of Pharmacy, Raichur 584 102, India
***Department
of Biochemistry, K. S. Hegde Medical Academy, Mangalore 574 162, India
****Department
of Chemistry, SAMbalpur University, Jyoti Vihar 768
019, India
(Received 21 April 2009, revised 13
September 2010)
Several 5-thio-substituted tetrazole derivatives were efficiently synthesized by a three-step process. The substituted
tetrazol-5-thiol, nAMely, 1-benzyl-1H-tetrazole-5-thiol
(2) was prepared by refluxing
commercially available benzyl isothiocyanate (1) with sodium azide in water. The second step was the synthesis of
1-benzyl-5-[(3-bromopropyl)thio]-1H-tetrazole
(3) by thioalkylation of
tetrazole-5-thiol 2 with
1,3-dibromopropane in tetrahydrofuran. Finally, the 5-thio-substituted
tetrazole derivatives 4a–i were prepared by condensation of 3 with the corresponding AMine or
thiol. The structures of the newly synthesized compounds were characterized by
NMR, LC/MS/MS, IR spectral data and elemental analysis. All the synthesized
compounds were screened for their antibacterial and antifungal activities.
Keywords: substituted thiol; tetrazole; 1,3-dibromopropane;
antibacterial; antifungal.
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J. Serb. Chem. Soc. 76 (2) 177–188 (2011)
UDC 547.856+542.913:667.281.1;
JSCS–4110; doi: 10.2298/JSC090225021P; Original scientific paper
Novel 2-phenyl-3-{4’-[N-(4”-AMinophenyl)carbAMoyl]-phenyl}-quinazoline-4(3H)one-6-sulphonic acidbased mono azo
reactive dyes
DIVYESH R. PATEL and KESHAV C. PATEL
Department of Chemistry, Veer Narmad South Gujarat
University, Surat 395 007, Gujarat, India
(Received 25 February 2009, revised 23
September 2010)
A series of new heterocyclic mono azo
reactive dyes 7a–m were prepared by diazotization of
2-phenyl-3-{4’-[N-(4”-AMinophenyl)carbAMoyl]-phenyl}-quinazoline-4(3H)-one-6-sulphonic acid (3) and coupling with various cyanurated
coupling components 6a–m and their dyeing performance on silk,
wool and cotton fibres was assessed. These dyes were found to give a variety of
colour shades with very good depth and levelness on the fibres. All the
compounds were identified by conventional method (IR and 1H-NMR) and elemental analyses. The percentage dye bath
exhaustion on different fibres was reasonably good and acceptable. The dyed
fibre showed moderate to very good fastness to light, washing and rubbing.
Keyword: quinazoline-4(3H)-one; mono azo reactive dyes; dyeing; fastness properties.
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J. Serb. Chem. Soc. 76 (2) 189–199 (2011)
UDC
547.93+547.47+546.33–38:*verapAMil; JSCS–4111; doi: 10.2298/JSC090619023P; Original scientific paper
Effect of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic
and 3,7,12-trioxo-5β-cholanoic
acids on verapAMil hydrochloride in biophysical–chemical model experiments
MIHALJ
M. POŠA, VALÉRIA J. GUZSVÁNY*, MOMIR M. MIKOV and JANOŠ J. ČANADi*
Department
of Pharmacy, Faculty of Medicine, Hajduk Veljkova 3, University of Novi Sad,
21000 Novi Sad, Serbia
*Department of Chemistry, Faculty
of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi
Sad, Serbia
(Received 19 June, revised 13 September
2010)
It is known that certain bile acids have
a promotive effect on the action of some drugs. Special attention is paid to
bile acids having oxo groups instead of OH groups in the steroid skeleton of
their molecule, since these derivatives have a lower hemolytic potential
(membrane toxicity). This study exAMined the effects of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic
acid (7-oC) and 3,7,12-trioxo-5β-cholanoic
acid (3,7,12-toC) on the adsorption of verapAMil hydrochloride on activated
carbon (model of the cell membrane). The interaction was followed by measuring
the effect of verapAMil on the functional dependence between the spin-lattice
relaxation time T1
(protons of the C18 angular group of the bile acid molecule) and the bile acid
concentration in deuterated chloroform (model of the cell membrane lipid
phase). Whether a depot effect of verapAMil exists when 7-oC and 3,7,12-toC (in
the form of methyl esters) are present in chloroform was also investigated. It
was found that 7-oC
exhibited a significant effect in the experiments with verapAMil, whereas
3,7,12-toC showed no difference of the measured parAMeters with respect to the
control. This indicates that bile acid molecules should have OH groups bound to
the steroid nucleus, in order to exhibit an effect on the monitored
physico–chemical parAMeters of verapAMil.
Key words: Bile acid oxo derivatives; verapAMil; spin-lattice
relaxation time.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2) 201–210 (2011)
UDC
547.722+546.17:542.913+547.78+547.861.3:579.8; JSCS–4112; doi: 10.2298/JSC100324013M; Original scientific paper
Synthesis and
biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type
of anti-Helicobacter pylori heterocycles
MOHAMMAD
HASSAN MOSHAFI, AZADEH YAHYA-MEYMANDI*, SEYED ESMAEIL SADAT-EBRAHIMI*, SAEED
EMAMI**,
MARYAM NAKHJIRI*, FARIDEH SIAVOSHI***, MARYAM OMRANI***, MOHSEN VOSOOGHI*,
ESKANDAR ALIPOUr****, ABBAS SHAFIEE* and ALIREZA FOROUMADI*
Department
of Pharmaceutical Microbiology, Faculty of Pharmacy, Kerman University of
Medical Sciences, Kerman, Iran
*Department of Medicinal Chemistry, Faculty of Pharmacy
and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
**Department of Medicinal Chemistry and Pharmaceutical
Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical
Sciences, Sari, Iran
***Microbiology Department, Faculty of Sciences,
University of Tehran, Tehran, Iran
****Department of Chemistry, IslAMic Azad University,
Tehran-North Branch, Zafar St., Tehran, Iran
(Received 24 March, revised 18 October
2010)
In order to find new and potent drug
candidates for the treatment of Helicobacter
pylori infections‚ in this
study attention was focused on the synthesis and anti-H. pylori activity
of a series of 5-(5-nitrofuran-2-yl)-1,3,4-thiadiazoles containing piperazinyl
functionality at the C-2 position of the
1,3,4--thiadiazole ring. The synthesis of
1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2--yl]piperazine derivatives 3a–h and pyrrolidine derivative 3i
was achieved with a versatile and efficient synthetic route via
2-chloro-5-(5-nitrofuran-2-yl)-1,3,4--thiadiazole. The inhibitory activity of
the new derivatives 3a–i
against twenty clinical H. pylori strains was evaluated by the disc
diffusion method and compared with the commercially available standard drug metronidazole. Resulting biological data indicated
that most compounds exhibited strong inhibitory activity even at doses lower
than 2 μg/disc (average zone of inhibition >20 mm) while metronidazole
had little or no growth inhibition at this dose. Compound 3c containing
the N-benzoylpiperazin-1-yl moiety showed the most potent inhibitory
activity.
Keywords: synthesis; 1,3,4-thiadiazole; 5-nitrofuran; antibacterial activity; Helicobacter pylori.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2) 211–220 (2011)
*Haberlea rhodopensis:577.121:57–188;
JSCS–4113; doi: 10.2298/JSC100324024B; Original scientific paper
GC–MS profiling of bioactive extracts from Haberlea
rhodopensis: an endemic resurrection plant
STRAHIL H. BERKOV, MILENA T. NIKOLOVA*, NEVENA I. HRISTOZOVA**, GEORGI
Z. MOMEKOV***, ILIANA I. IONKOVA*** and DIMITAR L. DJILIANOV*
AgroBio Institute, 8 Dragan
Tzankov Blvd., 1164-Sofia, Bulgaria
*Institute of Botany,
Bulgarian Academy of Sciences, 23 Acad. G. Bonchev Str., 1113-Sofia, Bulgaria
**Faculty of Biology, Sofia
University, 8 Dragan Tzankov Blvd., 1164-Sofia, Bulgaria
***Faculty of Pharmacy,
Medical University of Sofia, 2 Dunav Str., 1000- Sofia, Bulgaria
(Received 24 March, revised 6 July 2010)
GC–MS metabolic profiling of the apolar and
polar fractions from methanolic extracts of Haberlea rhodopensis
revealed more than one hundred compounds (AMino acids, fatty acids, phenolic
acids, sterols, glycerides, saccharides, etc.).
Bioactivity assays showed that the polar fractions possessed strong free
radical scavenging activity (IC50
= 19.95±14.11 μg ml-1 for fresh leaves and 50.04±23.16 μg
ml-1 for desiccated leaves), while both the polar and apolar
fractions failed to provoke any significant cytotoxic effects against the
tested cell lines. Five compounds possessing antiradical activity were
identified – syringic, vanillic, caffeic, dihydrocaffeic and p-coumaric
acids.
Keywords: Haberlea rhodopensis;
metabolites; free radical scavenging activity.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2)
221–233 (2011)
UDC
546.77–31+547.298.61:543.57:542.9+547.571+547.55; JSCS–4114; doi: 10.2298/JSC100208009N; Original scientific paper
Synthesis and characterization of oxomolybdenum(V) and
dioxomolybdenum(VI) complexes derived from N’-(2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide
Madhavan Nair Lekshmy HARIKUMARAN NAIR and DevakiAMma THANKAMANI
Department of Chemistry,
University College, ThiruvananthapurAM-695 034, India
(Received
8 February, revised 23 August 2010)
Several novel complexes of oxomolybdenum(V) and
dioxomolybdenum(VI) were synthesized with the Schiff base, N’-(2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide
(HL) derived from 3-methoxysalicylaldehyde and isonicotinohydrazide. The
complexes were characterized by elemental analyses, molar conductance and
magnetic susceptibility, as well as IR, 1H-NMR, FAB mass and UV–Vis
spectral studies. The complexes have the general formulae [MoO(L)XCl] and [MoO2(L)X], where X=NO3 or ClO4. The IR spectra of these
complexes indicate that the ligand HL acts as a monoanionic tridentate
chelating agent. The spectra indicate the monodentate mode of coordination for the nitrate and perchlorate groups. The X-ray
diffraction studies of [MoO(L)NO3Cl] correspond to an orthorhombic crystal lattice with
unit cell dimensions a = 15.49 Ĺ, b = 12.44 Ĺ and c = 10.11 Ĺ. All the complexes were found to have distorted
octahedral geometry. Thermal studies of the complex [MoO2(L)NO3] showed that it was stable
up to 240 °C, above which it started to decompose. The optimized geometry of
ligand and one of its complexes, [MoO(L)NO3Cl], have been obtained by a molecular mechanics
method. Antibacterial studies of the present complexes show that the
oxomolybdenum(V) complexes were more potent bactericides than the ligand and
the dioxomolybdenum(VI) complexes.
Keywords:
oxomolybdenum(V); dioxomolybdenum(VI); 3-methoxysalicylaldehyde
isonicotinoylhydrazone; thermal analysis; 3D modelling.
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J. Serb. Chem. Soc. 76 (2)
235–247 (2011)
UDC
546.712:548.7:543.42–74:547–327; JSCS–4115; doi:
10.2298/JSC100218012H;
Original scientific paper
The crystal structure and spectroscopic properties of catena-(2-methylimidazolium bis(μ2-chloro)aquachloromanganese(II))
BARBARA
HACHUŁA, MONIKA PĘDRAS, MARIA NOWAK*, JOACHIM KUSZ*, DANUTA PENTAK and JERZY BOREK
Institute
of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland
*Institute
of Physics, University of Silesia, 4 Uniwersytecka Street, 40-007 Katowice, Poland
(Received 18 February, revised 27
September 2010)
А novel manganese(II) coordination
polymer, catena-(2-methylimidazolium
bis(μ2-chloro)aquachloromanganese(II)),
{(C4H7N2)[MnCl3(H2O)]}n, was synthesized, structurally
characterized by FTIR spectroscopy and confirmed by single crystal X-ray
diffraction analysis. Thermogravimetric analysis and EPR spectroscopy of the
compound were also performed. The colourless crystals of the complex were
monoclinic, space group P21/c, with the cell parAMeters a = 11.298(2) Ĺ, b = 7.2485(14) Ĺ, c =
14.709(5) Ĺ, β = 128.861(18)°, V =
938.0(5) Ĺ3, Z = 4 and R1 = 0.03. The title compound
consisted of one-dimensional infinite anionic chains [MnCl3(H2O)]n
and isolated 2-methylimidazolium cations. The Mn(II) atom was octahedrally
coordinated to four bridging chloride anions (Mn–Cl = 2.5109(6) – 2.5688(7) Ĺ),
one terminal chloride anion (Mn–Cl = 2.5068(11) Ĺ) and a H2O
molecule (Mn–O = 2.2351(17) Ĺ). A three-dimensional layer structure was
constructed via hydrogen bonds and by weak π–π stacking interactions. A four-step thermal
decomposition occurred in the temperature range 25–900
°C under nitrogen.
Keywords: manganese(II) complex; 2-methylimidazole; X-ray crystal
structure; IR spectra; EPR spectra.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2)
249–261 (2011)
UDC
546.654.3+542.913:543.57:66.095.13/.14; JSCS–4116; doi:
10.2298/JSC100414025A;
Original scientific paper
Synthesis and spectroscopic
characterization of some lanthanide(III) nitrate complexes of ethyl
2-[2-(1-acetyl-2-oxopropyl)azo]-4,5-dimethyl-3-thiophenecarboxyate
CHEMPAKAM
JANARDHANAN ATHIRA, YESODHARAN SINDHU, MATHUNNI SUSAMMA SUJAMOL and KOCHUKITTAN MOHANAN
Department of Chemistry, University of Kerala,
Kariavattom CAMpus, Trivandrum-695 581, Kerala, India
(Received
14 April, revised 10 September 2010)
Ethyl
2-[2-(1-acetyl-2-oxopropyl)azo]-4,5-dimethyl-3-thiophenecarboxyate was synthesized by coupling diazotized
ethyl 2-AMino-4,5-dimethylthiophene-3-carboxylate with acetylacetone. Based on
various spectral studies and elemental analysis, an intrAMolecularly
hydrogen-bonded azo-enol structural form was assigned for the ligand. This
ligand is versatile in forming a series of lanthanide(III) complexes, viz., lanthanum(III), cerium(III),
praseodymium(III), neodymium(III), sAMarium(III) and gadolinium(III), which
were characterized through various spectral
studies, elemental analysis, magnetic susceptibility measurements, molar
conductance and thermal analysis. The spectral data revealed that the ligand
acted as a neutral tridentate, coordinating to the metal ion through one of the
azo nitrogen atoms, the ester carbonyl and the enolic oxygen of the
acetylacetone moiety, without deprotonation. Molar conductance values
adequately supported their non-electrolytic nature. The ligand and
lanthanum(III) complex were subjected to X-ray diffraction studies. In
addition, the lanthanum(III) complex underwent a facile transesterification
reaction on refluxing with methanol for a long period. The thermal behaviour of
the lanthanum(III) complex was also exAMined.
Keywords: azo derivative;
lanthanum(III) complex; molar conductance; XRD; transesterification; thermal analysis.
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2011. Cited by
J. Serb. Chem. Soc. 76 (2)
263–281 (2011)
UDC 615.214:547.95/.96:539.219; JSCS–4117; doi: 10.2298/JSC100806022A; Original scientific paper
QSAR–CoMSIA applied to antipsychotic drugs with their
dopAMine D2 and serotonine 5HT2A membrane receptors
SPERANTA AVRAM, DANIEL
DUDA-SEIMAN*, FLORIN BORCAN** and PETER WOLSCHANN***
University of Bucharest, Faculty
of Biology, Physiology and Biophysics Dept., 91–95 Spl. Independentei,
Bucharest-762015, Romania
*University of Medicine and
Pharmacy “Victor Babes” Timisoara, Clinic of Preventive Cardiology and
Cardiovascular Rehabilitation, 49 C.D. Loga Bvd., Timisoara-3000205, Romania
**West University Timisoara,
Faculty of Chemistry, Biology and Geography, Chemistry Dept., 16 Pestalozzi
Str., Timisoara-300115, Romania
***University of Vienna,
Institute for Theoretical Chemistry, 17 Währingerstrasse, Vienna-1090, Austria
(Received 6 August, revised 9 September 2010)
Antipsychotic drugs are psychiatric medication
primarily used to manage psychosis (e.g.,
delusions or hallucinations), particularly in schizophrenia and bipolar
disorder. First and second generations of antipshychotics tend to block
receptors in the brain's dopAMine pathways, but antipsychotic drugs encompass a
wide range of receptor targets. The inhibition constant, Ki, at the level of membrane receptors is a major determinant
of their pharmacokinetic behavior and, consequently, it can affect their
antipsychotic activity. Here, predicted inhibition constants, Ki for 71 antipsychotics,
already approved for clinical treatment, as well as representative new chemical
structures which exhibit antipsychotic activity, were evaluated using
3D-QSAR–CoMSIA models. Significant values of the cross-validated correlation q2 (higher than 0.70) and the
fitted correlation r2 (higher than 0.80) revealed that
these models have reasonable power to predict the biological affinity of the 15
new risperidone and 12 new olanzapine derivatives in interactions with dopAMine
D2 and serotonin 5HT2A receptors; these compounds are
suggested for further studies.
Keywords: antipsychotic;
CoMSIA; QSAR; membrane receptors; olanzapine; risperidone.
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J. Serb. Chem. Soc. 75 (2)
283–303 (2011)
UDC
546.151–128.2+546.48–128.4+544.723:546.57; JSCS–4118; doi: 10.2298/JSC100701026J; Original scientific paper
Processes of adsorption/desorption of iodides and cadmium cations onto/from Ag(111)
VLADIMIR D. JOVIĆ and BORKA M.
JOVIĆ
Institute for Multidisciplinary
Research, P.O. Box 33, 11030 Belgrade, Serbia
(Received 1 July, revised 23 August
2010)
In this work, the adsorption/desorption processes
of iodides and cadmium cations in the presence of iodides onto/from Ag(111)
were investigated. It was shown that both processes were complex, characterized
by several peaks on the cyclic voltAMmogrAMs (CVs). By PeakFit analysis of the
recorded CVs and subsequent fitting of the obtained peaks by the Frumkin
adsorption isotherm, the interaction
parAMeter (f) and the Gibbs energy of
adsorption (DGads) for each adsorbed phase were determined.
In the case of iodide adsorption, four peaks were characterized by negative
values of f, indicating attractive lateral interaction between the adsorbed
anions, while two of them possessed value of f < –4, indicating phase transition processes. The
adsorption/desorption processes of cadmium cations (underpotential deposition –
UPD of cadmium) in the presence of iodide anions was characterized by two main
peaks, each of them being composed of two or three peaks with negative values
of f. By the analysis of charge vs. potential dependences obtained
either from the CVs or current transients on potentiostatic pulses, it was
concluded that adsorbed iodides did not undergo desorption during the process
of Cd UPD, but becAMe replaced by Cd ad-atoms and remained adsorbed on top of a
Cd layer and/or in between Cd the ad-atoms.
Keywords: Ag(111); iodide adsorption; iodide
desorption; Cd underpotential deposition; phase transition.
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J. Serb. Chem. Soc. 76 (2)
305–315 (2011)
UDC 547.594+547.412.23:536.423.4+541.121:536.7;
JSCS–4119; doi:
10.2298/JSC090127020D;
Original scientific paper
Isothermal
vapour–liquid equilibria in cyclohexanone + dichloroalkane binary mixtures at
temperatures from 298.15 to 318.15 K
DANA
DRAGOESCU, ALEXANDRU BARHALA, MARIANA TEODORESCU and DANIELA CHISCAN
“Ilie Murgulescu” Institute of Physical Chemistry,
Splaiul Independentei 202, 060021
Bucharest, Romania
(Received 27 January, revised 21
September 2010)
The vapour pressures of binary mixtures of
cyclohexanone + dichloroalkane (1,3-dichloropropane and 1,4-dichlorobutane)
were measured at temperatures between 298.15 and 318.15 K. The vapour pressures
vs. liquid phase composition data
were used to calculate the activity coefficients of the two components and the
excess molar Gibbs energies GE for
the mixtures, using the Barker method and the Redlich–Kister, Wilson, NRTL and
UNIQUAC equations, taking into account the vapour phase imperfection in terms
of the 2nd
virial coefficient. No significant difference between the GE values obtained with these equations
was observed.
Keywords: vapour pressure; vapour–liquid equilibria; excess Gibbs energy; mixtures; cyclohexanone;
dichloroalkanes.
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2011. Cited by
Copyright &AMp; copy; SHD 2011.
February 20, 2011.
For more information contact: JSCS-info@shd.org.rs