JSCS Vol 69, No. 7
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Impresum |
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J.
Serb.Chem.Soc. 69 (7) 511–526 (2004) |
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The synthesis and
preliminary pharmacological evaluation of the racemic cis and trans
3-alkylfentanyl analogues
M. D. IVANOVIC, I. V. MICOVIC, S.
VUCKOVIC*, M. PROSTRAN*, Z. TODOROVIC*,
V. D. KIRICOJEVIC**, J. B. DJORDJEVIC*** and LJ. DOSEN-MICOVIC
Faculty of Chemistry, University of Belgrade, Studentski Trg 12-16,
Belgrade,
*Department of Clinical Pharmacology, Pharmacology and Toxicology, School of
Medicine, University of Belgrade,
Dr Subotica 1, P. O. Box 840, 11129 Belgrade,
**ICTM-Center for Chemistry, Njegoseva 12, Belgrade and
***Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Zemun,
Serbia and Montenegro
(Received 9 September,
revised 4 February 2004)
A general, five step method for the synthesis of
3-alkylfentanyl analogues (i.e., cis and trans
3-alkyl-4-anilidopiperidines 6.1–6.6) has been developed. The starting N-phenethyl-4-piperidone
1 was first converted into the cyclohexylimine derivative 2, a-deprotonated with butyllithium and the resulting imine anion
efficiently monoalkylated with primary and secondary alkyl halides. After mild
acid hydrolysis, the obtained 3-alkyl-4-piperidones 3.1–3.6 were
isolated in good yields (79–85 %), then condensed with aniline to form imines 4.1–4.6.
Subsequent reduction of the imines (LiAlH4/THF) yielded cis/trans
mixtures of 3-alkyl-4-anilinopiperidines 5.1–5.6. Quantitative
separation of the diastereoisomers by column chromatography of Al2O3
gave pure cis 5.1–5.6 (29–51 % yield) and trans 5.1–5.6
(19–27 % yield), with the cis/trans ratio in the range 7/3–6/4. The synthesis
was concluded by N-acylation of the purified 5.1–5.6, with propionyl
chloride, to afford cis and trans 3-alkyl-4-anilidopiperidines 6.1–6.6
(~95 % yield, as monooxalate salts). No
enatioseparation was attempted at any stage. The relative cis/trans
stereochemistry was provisionally assigned from the 1H-NMR spectra. Of the
twelve synthesized 3-alkylfentanyls, ten compounds (two known and eight novel
derivatives, all as the monooxalate salts) were preliminarily tested as
analgesics in rats, comparing the potency to fentanyl. Except for the known
(±)-cis-3-Me fentanyl 6.1cis, (8 × fentanyl), and the
novel (±)-cis-3-Et fentanyl 6.2cis, (1.5 × fentanyl), all
of the others were less active than fentanyl or inactive. Some tentative
conclusions on the structure-activity relationship (SAR) in this series of
derivatives have been made.
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J. Serb. Chem.
Soc. 69 (7) 527–532 (2004) |
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A facile synthesis of 10-methoxy-4,8-dinitro-6H-benzothieno[2,3-c]chromen-6-one
FREDDY H. HAVALDAR, SANJAY BHISE and SANDEEP
BURUDKAR
Nadkarny-Sacasa Research
Laboratory, Department of Chemistry, St. Xavier's College, Mumbai 400 001,
India
(Received 2 October
2003, revised 9 February 2004)
3-Methoxy-5-nitrobenzaldehyde undergoes
Knoevenagel reaction with malonic acid to give 3-methoxy-5-nitrocinnAMic acid (I).
Treatment of I with thionyl chloride yielded
3-chloro-5-methoxy-7-nitrobenzo[b]thiophene-2-carbonyl chloride (II)
in 45 % yield. The reaction of II with 2-nitrophenol in benzene gave
2-nitrophenyl 3-chloro-5-methoxy-7-nitrobenzo[b]thiophene-2-carboxylate
(IIIa) in 65 % yield. Finally, dehydrochlorinative photocyclization of
IIIa in acetone in the presence of the base triethylAMine afforded
10-methoxy-4,8-dinitro-6H-benzothieno[2,3-c]chromen-6-one (IVa).
Thus, a series of derivatives IVa-i were synthesized in excellent
yields. The structures of the obtained products were characterized by IR and
1H-NMR spectroscopy, as well as elemental analysis. Their purity was
ascertained by chromatographic analysis. All the compounds were tested for
their antibacterial activity against S. aureus, E. coli, B.
subtilis and S. typhosa.
Keywords: coumarin, cinnAMic acid, antibacterial activity, photolytic
cyclization.
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J. Serb. Chem.
Soc. 69 (7) 533–540 (2004) |
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IgG binding of mugwort pollen allergens and
allergoids exposed to simulated gastrointestinal conditions measured by a
self-developed ELISA test
NATALIJA DJ. POLOVIC, TANJA D. CIRKOVIC–VELICKOVIC, MARIJA DJ.
GAVROVIC-JANKULOVIC, LIDIJA BURAZER*,
DANICA DJERGOVIC-PETROVIC*, OLGA VUCKOVIC* and RATKO M. JANKOV
Faculty of Chemistry,
Studentski trg 16, 11000 Belgrade and
*Institute for Immunology and Virology, Torlak, Vojvode Stepe 458, 11221
Belgrade, Serbia and Montenegro
(Received 18 December
2003)
This study considers the influence of exposure to simulated gastrointestinal
conditions (saliva, gut, intestine and acidic conditions of the gut) on IgG
binding of unmodified allergens and three types of LMW allergoids of Artemisia
vulgaris pollen extract obtained by means of potassium cyanate, succinic
and maleic anhydride. It also concerns the optimization of a self-developed
ELISA assay for comparison of the specific IgG binding of mugwort pollen
extract and modified mugwort pollen derivatives. The ELISA was conducted with a
mugwort pollen extract coupled to the plate, using the sera from 12
mugwort-pollen allergic patients. The exposure to saliva fluid for 2 min did
not influence the IgG binding properties of allergens and allergoids. Exposure
of mugwort pollen allergens and LMW allergoids to the acidic conditions of the
gut did not drAMatically change their IgG binding properties. By exposing
mugwort pollen extract and LMW derivatives to the SGF conditions for 1 h, the
percent of IgG binding epitopes was reduced to a half of its starting value in
the extract and to about 30 % in all the allergoid sAMples. After prolonged
exposure only the carbAMyl derivative showed reduced IgG binding. Changes of
the IgG binding potential of all four sAMples after exposure in SIF followed a
similar pattern.
Keywords: simulated gastrointestinal conditions, Artemisia vulgaris,
mugwort, pollen, allergoid.
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J. Serb. Chem.
Soc. 69 (7) 541–547 (2004) |
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SHORT COMMUNICATION
The influence of
transition and heavy metal ions on ATP-ases activity in rat synaptic plasma
membranes
LJUBICA VUJISIC, DANIJELA KRSTI*, KATARINA
KRINULOVIC and VESNA VASIC
Laboratory of Physical
Chemistry, Vinca Institute of Nuclear Sciences, P. O. Box 522 and
*School of Medicine, University of Belgrade, Visegradska 26, 11000 Belgrade,
Serbia and Montenegro
(Received 10 October
2003, revised 15 January 2004)
The influence of transition metal (Cu2+,
Zn2+, Fe2+ and Co2+) and heavy metal ions (Hg2+,
Pb2+ and Cd2+) on the activities of Na+/K+-ATPase
and Mg2+-ATPase isolated from rat synaptic plasma membranes (SPM)
was investigated. The aim of the study was to elucidate the inhibition of both
ATPase activities by exposure to the considered metal ions as a function of
their affinity to bind to the –SH containing ligand L-cysteine, as a model
system. The half-maximum inhibitory activities (IC50) of the
enzymes were determined as parAMeters of rectangular hyperbolas and correlated
with the stability constant (Ks) of the respective
metal-ion-L-cysteine complex. The linear Dixon plots indicate equilibrium
binding of the investigated ions to both enzymes.
Keywords: transition metal ions, heavy metal ions, Na+/K+-ATPase,
Mg2+-ATPase, inhibiton.
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J. Serb. Chem.
Soc. 69 (7) 549–553 (2004) |
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Equienergetic chemical trees
VLADIMIR BRANKOV, DRAGAN STEVANOVIC and IVAN
GUTMAN*
Department of Mathematics, Faculty of Science, University of Nis,
Visegradska 33, 18000 Nis and
*Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac,
Serbia and Montenegro
(Received 26 January
2004)
The energy E(G) of a graph G
is the sum of the absolute values of the eigenvalues of G. Two graphs, G1
and G2, are said to be equienergetic if E(G1)
= E(G2). We report here the results of the search for
pairs of equienergetic acyclic molecular graphs (chemical trees) with the sAMe
number n of vertices. There are very few such pairs. The smallest has n
= 9 and pertains to 3,3-diethylpentane and 3-methyloctane. Among the chemical
trees with n < 18, only five more such pairs and a triplet were
found.
Keywords: energy of graph, total p-electron
energy, chemical trees, equienergetic graphs.
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J. Serb. Chem.
Soc. 69 (7) 555–561 (2004) |
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Cretaceous-Tertiary boundary deposits in
Denmark: A diachroneity
PAVLE I. PREMOVIC
Laboratory for Geochemistry,
Cosmochemistry and Astrochemistry, University of Nis, P. O. Box 91, 18000 Nis,
Serbia and Montenegro
(Received 8 January
2004)
The lateral distribution of predominantly
terrestrial kerogen or humics enriched with copper(II) porphyrins (Cu-P) across
the Danish marine basin implies that the alleged Cretaceous-Tertiary (KT)
boundary deposits in western Denmark (at the Nye Kløv/Dania locations) were
probably formed by erosion/emplacement of the boundary clay (Fiskeler) in
eastern Denmark by marine currents, as originally proposed by Hulteberg.
Keywords: diachroneity, kerogen, copper(II) porphyrins, Cretaceous-Tertiary,
Fiskeler, boundary clay.
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J. Serb. Chem.
Soc. 69 (7) 563–569 (2004) |
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Study of sulfur dioxide adsorption on Y zeolite
IOAN-CEZAR MARCU and IOAN SĂNDULESCU
Department of Chemical Technology and Catalysis, Faculty of Chemistry,
University of Bucharest,
Bd. Regina Elisabeta No. 4-12, 030018 Bucharest, Romania
(Received 30 September
2003, revised 26 January 2004)
Sulfur dioxide adsorptive properties of Y
zeolite, the structure of which was confirmed by XRD, were investigated at
temperatures within the 25–200 ºC range and sulfur dioxide concentrations
between 0.9 to 6 % (vol./vol.). It was found that this sorbent possesses a
relatively high adsorption capacity. The Y zeolite did not lose its activity
during 20 adsorption-desorption-regeneration cycles. The manner in which sulfur
dioxide is adsorbed on Y type zeolite was also investigated by analyzing the
sAMple with and without adsorbed SO2, using IR spectroscopy, as well
as total and Lewis acidity measurements. The sulfur dioxide molecule is
probably adsorbed by hydrogen bonding to one or two conveniently positioned
surface hydroxyl groups.
Keywords: sulfur dioxide, adsorption, Y zeolite, desulfurization.
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J.Serb.Chem.Soc.
69(7)571–574(2004) |
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High-performance liquid chromatographic separation of surface flavonoid
aglycones in Artemisia annua L.
and Artemisia vulgaris L.
MILENA NIKOLOVA, RENETA GEVRENOVA* and STEPHANKA
IVANCHEVA
Department of Applied Botany, Institute of Botany, Bulgarian Academy of
Sciences, bl. 23, “Acad. G. Bonchev” str., 1113 Sofia, Bulgaria and
*Department of Pharmacognosy, Faculty of Pharmacy, Medical University – Sofia,
2, Dunav str., 1000 Sofia, Bulgaria
(Received 5 November
2003)
External flavonoid aglycones from Artemisia
annua L. and Artemisia vulgaris L. were analyzed by the HPLC method.
The mobile phase was composed of t-butanol-methanol-20 mmol l-1
phosphate buffer, pH 3.22. The linear gradient elution method within 22 min was
applied. The main aglycones in A. annua and A. vulgaris are
methyl ethers of quercetagetin and quercetin. Quercetagetin 3,6,7-trimethyl
ether in A. annua and quercetin 3,7,3’-trimethyl ether in A. vulgaris
are the most abundant compounds.
Keywords: Artemisia annua, Artemisia vulgaris, HPLC, flavonoid aglycones,
quercetagetin 3,6,7-trimethyl ether, quercetin 3,7,3’-trimethyl ether.
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J. Serb. Chem.
Soc. 69 (7) 575–580 (2004) |
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Potentiometric stripping analysis of lead and cadmium leaching from dental
prosthetic materials and teeth
RUZICA S. NIKOLIC, BILJANA M. KALICANIN* and
GORAN M. NIKOLIC**
1Department of Chemistry, Faculty of Sciences, University of Nis,
Visegradska 33, 18000 Nis,
*Faculty of Technology, University of Nis, Bulevar oslobodjenja 124, 16000
Leskovac and
**Department of Chemistry, Faculty of Medicine, University of Nis, Brase
Taskovic 81, 18000 Nis, Serbia and Montenegro
(Received 4 November
2003, revised 26 January 2004)
Potentiometric stipping analysis (PSA) was
applied for the determination of lead and cadmium leaching from dental
prosthetic materials and teeth. The soluble lead content in finished dental
implants was found to be much lower than that of the individual components used
for their preparation. Cadmium was not detected in dental implants and
materials under the defined conditions. The soluble lead and cadmium content of
teeth was slightly lower than the lead and cadmium content in whole teeth (w/w)
reported by other researchers, except in the case of a tooth with removed
AMalgAM filling. The results of this work suggest that PSA may be a good method
for lead and cadmium leaching studies for investigation of the biocompatibility
of dental prosthetic materials.
Keywords: PSA, lead leaching, cadmium leaching, dental prosthetic materials,
teeth.
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J. Serb. Chem.
Soc. 69 (7) 581–599 (2004) |
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Axial dispersion of the liquid phase in a three-phase
Karr reciprocating plate column
LJUBISA B. NIKOLIC, VESNA D. NIKOLIC, VLADA B.
VELJKOVIC, MIODRAG L. LAZIC and DEJAN U. SKALA*
Faculty of Technology, Bulevar oslobo|enja 124, 16000 Leskovac and
*Faculty of Technology and Metallurgy, Karnegijeva 4, 11000 Belgrade, Serbia
and Montenegro
(Received 27 May 2003,
revised 2 February 2004)
The influence of the gas flow rate and vibration
intensity in the presence of the solid phase (polypropylene spheres) on axial
mixing of the liquid phase in a three phase (gas-liquid-solid) Karr reciprocating
plate column (RPC) was investigated. Assuming that the dispersion model of
liquid flow could be used for the real situation inside the column, the
dispersion coefficient of the liquid phase was determined as a function of
different operating parAMeters. For a two-phase liquid-solid RPC the following
correlation was derived:
DL = 1.26(Af)1.42 UL0.51
eS0.23
and a similar equation could be applied with ±
30 % confidence for the calculation of axial dispersion in the case of a
three-phase RPC:
DL = 1.30(Af)0.47 UL0.42
UG0.03eS-0.23
Keywords: Karr reciprocating plate column,
three-phase column, axial dispersion, residence time distribution, dispersion
model.
Copyright &AMp; copy; SHD 2004.
October 8, 2004.
For
more information contact: SHD@tmf.bg.ac.yu