JSCS Vol 69, No. 11
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Editor’s Note
This issue is dedicated to Professor Zivorad M.
Cekovic, corresponding member of the Serbian Academy of Sciences and Arts on
the occasion of his 70th birthday and in recognition of his
extraordinary contributions to science, particularly organic chemistry,
development of the Faculty of Chemistry, University of Belgrade, as well as the
Serbian Chemical Society. The papers are contributions of Professor Cekovic’s
colleagues and former students. Publication of this issue is financially
supported by the Faculty of Chemistry, University of Belgrade and Institute of
Chemistry, Technology and Metallurgy – Center for Chemistry. Guest editor of
this issue is Professor Radomir N. Saicic
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J. Serb. Chem. Soc. 69 (11) 839–842 (2004) |
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This issue of the Journal of the Serbian Chemical Society is
dedicated to Professor Živorad Čeković and his outstanding scientific and
professional activities, on the occasion of his 70th birthday. Professor
Čeković has given significant contributions to the science and teaching of
modern organic chemistry, particularly at the Department of Chemistry,
University of Belgrade. Therefore, it is my privilege and great pleasure, as
one of his university teachers and afterwards for many years his colleague and
close friend, to give a short summary of Professor Čeković’s professional life
on the occasion of his important and nice life jubilee.
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J.Serb.Chem.Soc.
69 (11) 843–854(2004) |
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REVIEW
Molecular modeling of fentanyl analogs
LJILJANA DOSEN-MICOVIC
Faculty of Chemistry,
University of Belgrade, P.O. Box 158, 11000 Belgrade and Center for Chemistry,
ICTM, Belgrade, Serbia and Montenegro
(Received 30 June 2004)
Fentanyl is a highly potent and clinically
widely used narcotic analgesic. A large number of its analogs have been
synthesized, some of which (sufentanil and alfentanyl) are also in clinical
use. Theoretical studies, in recent years, afforded a better understanding of
the structure-activity relationships of this class of opiates and allowed
insight into the molecular mechanism of the interactions of fentanyl analogs
with their receptors. An overview of the current computational techniques for
modeling fentanyl analogs, their receptors and ligand-receptor interactions is
presented in this paper.
Keywords: fentanyl analogs, molecular modeling, m-receptor, ligand-receptor
interactions.
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J. Serb. Chem.
Soc. 69 (11) 855–859 (2004) |
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SHORT COMMUNICATION
Synthesis of the 4’-desmethoxy analogue of
RU79115
BRANISLAV MUSICKI, ANNE-MARIE PERIERS, NICOLE TESSOT and MICHEL KLICH
Medicinal Chemistry,
Aventis Pharma, 102 route de Noisy, 93235 Romainville Cedex, France
(Received 22 March 2004)
The synthesis, and
biological activity in vitro of the 4’-desmethoxy analogue (3) of RU
79115 (2) is described. Comparison of the biological activity of the two
analogues clearly indicated the importance of the 4’-methoxy group in
conferring good gyrase B inhibitory activity as well as antibacterial activity.
Keywords: structure-activity, inhibitor, gyrase B, antibacterial, sugar, L-arabinose,
coumarin.
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J. Serb. Chem.
Soc. 69 (11) 861–869 (2004) |
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Synthesis of 5-azaandrostane-3b,17b-diol
protected at the 17b-hydroxyl group
VLADIMIR D. PAVLOVIC*,** MILAN M.
DABOVIC**, SASA MARTINOVIC**, LJUBINKA B. LORENC*,** and JAROSLAV
KALVODA***
*Faculty of Chemistry,
University of Belgrade, Studentski trg 12–16, P.O. Box 158, 11001 Belgrade,
**Center for Chemistry, ICTM, Njego{eva 12, P.O. Box 473, 11001 Belgrade,
Serbia and Montenegro and
***Leimgrubenweg 21 CH-4102, Binningen, Switzerland
(Received 1 July 2004)
In the present paper, the preparation of 3b-hydroxy-17b-dimethyl-tert-butylsilyloxy-5-azaandrostane
(15) in fourteen steps is described. B-nor-17-oxoandrost-5-en-3b-yl acetate (1) was used as the starting material, which
was transformed to the key intermediate of the synthesis, B-nor-17b-dimethyl-tert-butylsilyloxyandrost-4-en-3b-yl acetate (7).
Keywords: 5-azasteroids, B-nor-17-oxoandrost-5-en-3b-yl acetate, 3b-hydroxy-17b-dimethyl-tert-butylsilyloxy-5-azaandrostane.
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J. Serb. Chem.
Soc. 69 (11) 871–875 (2004) |
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SHORT COMMUNICATION
Allosteric regulation of small-molecule binding
to aptAMers
MILAN N. STOJANOVIC
Department of Medicine, Columbia University, Box
84, 650W 168th Street, New York, NY 10032
(Received 1 July 2004)
Modular aptAMeric sensors for oligonucleotides
were constructed by combining molecular beacon stem-loops and malachite green
aptAMers. These sensors were designed so that oligonucleotides complementary to
the stem-loop region accomplish the release of malachite green from its binding
module. The oligonucleotides that bound to both loop and stem caused efficient
release of the dye. While this sytem is not suitable for single-mismatch
detection, it represents proof-of-concept for drug delivery components of
autonomous therapeutic devices on a molecular scale.
Keywords: aptAMers, allosteric control, fluorescence, malachite.
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J. Serb. Chem.
Soc. 69 (11) 877–882 (2004) |
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Geometry and conformations of benzenecarboxylic
acids
ZORAN MARKOVIC, DALIBOR BADJUK and IVAN GUTMAN
Faculty of Science,
University of Kragujevac, P.O. Box 60, 34000 Kragujevac, Serbia and Montenegro
(Received 6 April 2004)
The geometry, conformations and energy of mono-,
di-, and tri-carboxylic derivatives of benzene were studied by means of the AM1
molecular-orbital method. Whereas the species having no carboxylic groups in
the ortho-position (benzoic, isophthalic, terephthalic, and trimesic
acids) are planar in all their (stable) conformations, those possessing
carboxylic groups in the ortho-position (phthalic,
1,2,3-benzenetricarboxylic, and 1,2,4-benzenetricarboxylic acids) assume a
non-planar geometry, with one carboxyl group almost orthogonal to the plane of
the benzene ring. Various rotAMers of each of the studied benzenecarboxylic
acids have nearly the sAMe energy.
Keywords: benzenecarboxylic acids, phthalic acid, trimesic acid,
conformation, rotAMer.
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J. Serb. Chem.
Soc. 69 (11) 883–886 (2004) |
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SHORT COMMUNICATION
Flavonoids from flowers
of Cephalaria pastricensis and their antiradical activity
DEJAN GODJEVAC, VLATKA VAJS, NEBOJSA MENKOVIC*,
VELE TESEVIC**, PEDJA JANACKOVIC*** and
SLOBODAN MILOSAVLJEVIC**
Institute of Chemistry,
Technology and Metallurgy, Njegoseva 12, 11000 Belgrade,
*Institute for Medicinal Plant Research “Dr. Josif Pancic”, Tadeusaa Koscuska
1, 11000 Belgrade,
**Faculty of Chemistry, Studentski trg 16, P.O. Box 158, 11000 Belgrade and
***Faculty of Biology, Studentski trg 16, 11000 Belgrade, Serbia and Montenegro
(Received 25 June 2004)
Two flavonoid glycosides 1 and 2
having the luteolin structure were isolated from flowers of the endemic plant
species Cephalaria pastricensis. They were identified by 1H
and 13C NMR, as well as UV/Vis spectroscopy. The structures of 1
and 2 were also confirmed by the spectral data of aglycones and TLC of
the sugars obtained after acid hydrolysis. Flavones 1 and 2 showed
significant antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH)
assay.
Keywords: Cephalaria pastricensis, luteolin 7-O-glucoside, luteolin
7-O-arabino(1-6)glucoside, antiradical activity, DPPH assay.
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J. Serb. Chem.
Soc. 69 (11) 887–899 (2004) |
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Steric effects on the rate of hydrolysis by palladium(II) complexes of the
C-terminal AMide bond in a series of
methionine-containing dipeptides AcMet-Aa
T. WADE JOHNSON and NENAD M. KOSTIC
Department of Chemistry,
Iowa State University, Ames, IA 50011, USA
(Received 3 July 2004)
A series of N-acetylated, methionine-containing
dipeptides designated AcMet-Aa containing various C-terminal AMino acids
designated Aa are hydrolyzed in aqueous solution at 50 ºC and 0.95 < pD <
1.10 in the presence of three cis-[Pd(L)(H2O)2]2+
complexes, in which L are bidentate ligands en, Me4en, and 3-OH-dtco. The
reactions were monitored by 1H-NMR spectroscopy. The rate constant
for hydrolytic cleavage of the Met-Aa bond decreases as the steric bulk of the
AMino acid Aa increases. Correlations to Taft’s Es values
were made. The substituents on a-C and b-C atoms lower the rate constant most, those on the g-C atom lower it less, and those on the d-C have no detectable effect. Partial selectivity for leaving
AMino acid Aa is attributed to differences in the volume of the side chain and
to discrimination between leaving groups of similar volume but different
branching patterns.
Keywords: selective
cleavage, kinetics, peptides, methionine, palladium(II).
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J.Serb. Chem.
Soc. 69 (11) 901–907 (2004) |
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Protein covalent modification by biologically active quinones
DUSAN SLADIC*, IRENA NOVAKOVIC**, ZORAN VUJCIC*,
TATJANA BOZIC*, NATASA BOZIC**, DRAGANA MILIC*, BOGDAN SOLAJA* and MIROSLAV J.
GASIC*,**
*Faculty of Chemistry, University of Belgrade,
Studentski trg 12-16, P.O. Box. 158, 11001 Belgrade and
**Institute for Chemistry, Technology and Metallurgy, Department of Chemistry,
Njegoseva 12, P.O. Box 473, 11001 Belgrade, Serbia and Montenegro
(Received 5 July 2004)
The avarone/avarol quinone/hydroquinone couple
shows considerable antitumor activity. In this work, covalent modification of b-lactoglobulin by avarone and its derivatives as well as by the
synthetic steroidal quinone 2,5(10)-estradiene-1,4,17-trione and its
derivatives were studied. The techniques for studying chemical modification of b-lactoglobulin by quinones were: UV/Vis spectrophotometry, SDS
PAGE and isoelectrofocusing. SDS PAGE results suggest that polymerization of
the protein occurs. It could be seen that the protein of 18 kD gives the bands
of 20 kD, 36 kD, 40 kD, 45 kD, 64 kD and 128 kD depending on modification
agent. The shift of the pI of the protein (5.4) upon modification toward lower
values (from pI 5.0 to 5.3) indicated that lysine AMino groups are the
principal site of the reaction of b-lactoglobulin with the
quinones.
Keywords: quinone, avarone, steroidal quinones, b-lactoglobulin, covalent modification.
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J. Serb. Chem.
Soc. 69 (11) 909–918 (2004) |
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Thionation of N-methyl- and N-unsubstituted thiazolidine
enAMinones
RADE MARKOVIC*,**, ALEKSANDAR RASOVIC**,
MARIJA BARANAC*,**, MILOVAN STOJANOVIC**, PETER J. STEEL*** and
STANKA JOVETIC****
*Faculty of Chemistry,
University of Belgrade, Studentski trg 16, P.O. Box 158, 11001 Belgrade, Serbia
and Montenegro
**Center for Chemistry ICTM, P.O. Box 815, 11000 Belgrade, Serbia and
Montenegro,
***Department of Chemistry, University of Canterbury, P.O. Box 4800,
Christchurch, New Zealand, and
****Department of Chemistry, Faculty of Science, University of Novi Sad, Trg D.
Obradovica 3, Novi Sad, Serbia and Montenegro
(Received 21 July 2004)
The potential of directional non-bonded 1,5-type
S...O interactions to initiate the incipient stage of an in situ
rearrangement of N-unsubstituted thiazolidine enAMinones to
functionalized 1,2-dithioles has been demonstrated. The spectral
characteristics, as well as X-ray structural analysis of a selected rearranged
product, indicate that a dynAMic interconversion occurs in solution between the
1,2-dithiole and the 3,3al4,4-trithia-1-azapentalene bicylic form. The lack
of the rearrangement in the case of a N-methyl substituted enAMinone
precursor is attributed to an unfavorable methyl migration in the last reaction
step.
Keywords: thiazolidine, enAMinone, Lawesson’s reagent, 1,2-dithiole, 3,3al4,4-trithia-1-azapentalene.
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J. Serb. Chem.
Soc. 69 (11) 919–922 (2004) |
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PRELIMINARY COMMUNICATION
7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecane-3-carboxylic
acid derivatives and their antimalarial activity
IGOR OPSENICA, NATASA TERZIC, DEJAN OPSENICA,
WILBUR K. MILHOUS* and BOGDAN SOLAJA**
Institute of Chemistry,
Technology and Metallurgy, Belgrade, Serbia and Montenegro,
*Devision of Experimental Therapeutics, Walter Reed Army Institute of Research,
Washington, DC 20307-5100, USA and
**Faculty of Chemistry, University of Belgrade, P.O. Box 158, 11001 Belgrade,
Serbia and Montenegro
(Received 27 May 2004)
Several C2 symmetrical mixed tetraoxanes were
prepared starting from a gemdihydroperoxide and a ketone. The obtained
tetraoxanes showed pronounced antimalarial activity against P. falciparum
chloroquine resistant W2 and chloroquine susceptible D6 strains, with N-(2-dimethylAMino)ethyl-7,8,15,16-tetraoxa-dispiro[5.2.5.2]
hexadecane-3-carboxAMide being as active as artemisinin.
Keywords: mixed tetraoxane, malaria, Plasmodium falciparum,
gem-dihydroperoxide.
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J. Serb. Chem.
Soc. 69 (11) 923–940 (2004) |
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Preserved precursors in Pumpherston
shale kerogen revealed by oxidative degradation
S. BAJC, A. AMBLÈS* and D. VITOROVIC*
Center of Chemistry,
Institute of Chemistry, Technology and Metallurgy, Njegoseva 12, 11000
Belgrade, Serbia and Montenegro
*Laboratoire de Chimie UMR-CNRS 6514, 40, Av. du Recteur Pineau, 86022
Poitiers, France
(Received 6 December
2003)
An optimised stepwise alkaline permanganate
degradation was shown to have potentials in elucidating the genesis pathway and
the origin of kerogens, and, more specifically, to reveal preserved precursors
in a kerogen matrix. Thus, Pumpherston shale kerogen, used as the substrate in
this study, was found to be of mixed origin, i.e., to contain both
inherited resistant algal structures (B. braunii A and B algaenans), as
well as resistant biomacromolecular components of continental flora (cutans).
It is suggested that this kerogen or parts of it were formed by the selective
preservation pathway.
Keywords: kerogen, Pumpherston shale, oxidative degradation, preserved
precursors.
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J. Serb. Chem.
Soc. 69 (11) 941–947 (2004) |
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Electrochemical
chlorination of some 5-unsaturated steroids
SMILJKA MILISAVLJEVIC and RASTKO D. VUKICEVIC*
Technical Faculty,
Kosovska Mitrovica, University of Pristina, Kneza Milosa 7, 28000 Kosovska
Mitrovica and
*Department of Chemistry, Faculty of Science, University of Kragujevac, R.
Domanovica 12, P.O. Box 60, 34000 Kragujevac, Serbia and Montenegro
(Received 24 May 2004)
Five 5-unsaturated steroids were subjected to
constant current electrolysis (50 mA) in a dichloromethane solution of
tetraethylAMmonium chloride in an undivided electrolytic cell at room
temperature, using a graphite stick as the anode and a cooper spiral as the
cathode. The addition of electrochemically generated elemental chlorine onto
the double bond of cholesterol derivatives (5-cholestene, cholesteryl acetate,
cholesteryl benzoate and 3-chloro-5-cholstene) gave the corresponding 5a,6b-dichlorosteroids, in
good yields (70–73 %). The obtained compounds (5a,6b-dichlorocholestane, 5a,6b-dichlorocholestane-3b-yl acetate, 5a,6b-dichlorocholestane-3b-yl benzoate and 3b,5a,6b-trichlorocholestane)
were characterized by physical and spectral data (IR, 1H–NMR and 13C–NMR).
However, under the sAMe reaction conditions, cholesterol produced a mixture of
products from which the expected dichloro derivative (3b-hydroxy-5a,6b-dichlorocholestane) could not be isolated. This compound was
prepared by alkaline hydrolysis of 5a,6b-dichlorocholestan-3b-yl acetate and 5a,6b-dichlorocholestan-3b-yl benzoate in methanol.
Keywords: electrolysis, electrochemical chlorination, 5-unsaturated
steroids, 5a,6b-dichlorosteroids.
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J. Serb. Chem.
Soc. 69 (11) 949–953 (2004) |
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SHORT COMMUNICATION
Kinetics of the reaction of 5-substituted orotic acids with
diazodiphenylmethane
BRATISLAV Z. JOVANOVIC, FATHI H. ASSALEH
and ALEKSANDAR D. MARINKOVIC
Faculty of Technology
and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3503, 11120
Belgrade, Serbia and Montenegro
(Received 3 August 2004)
Rate konstants for the reaction of eight
5-substituted orotic acids with diazodiphenylmethane (DDM) in dimethylformAMide
(DMF) were determined at 30 ºC by the known spectrophotometric method. The
determined rate constants were correlated with the equations:
log k2 = as1 + bsR + h
log k2 = as1 + bsR + yn + h
to detect the presence and investigate the
influence of both electrical and steric substituent effects. The obtained
results show that the electrical effect (the localized – field and delocalized
– resonance) is predominant and that the steric effect, althought present, is
releatively small in this reaction.
Keywords: orotic acids, diazodiphenylmethane, reaction kinetics
dimethylformAMide.
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J. Serb. Chem.
Soc. 69 (11) 955–968 (2004) |
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The synthesis and
pharmacological evaluation of (±)-2,3-seco-fentanyl analogues
M. D. IVANOVIC, I. V. MICOVIC, S. VUCKOVIC* M.
PROSTRAN* Z. TODOROVI*, E. R. IVANOVIC**, V. D. KIRICOJEVIC*** J. B.
DJORDJEVIC**, and LJ. DOSEN-MICOVIC**
Faculty of Chemistry,
University of Belgrade, Studentski trg 12–16, 11000 Belgrade
*Department of Clinical Pharmacology, Pharmacology and Toxicology, School of
Medicine, University of Belgrade,
Dr Subotica 1, P.O. Box 840, 11129 Belgrade,
**Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080, Zemun,
***ICTM-Center for Chemistry, Njegoseva 12, 11000 Belgrade, Serbia and
Montenegro
(Received 24 May 2004)
An efficient, five-step synthetic approach to
various acyclic 1,3-diAMines has been developed and applied to the preparation
of a novel class of open-chained fentanyl analogues. The acyclic derivatives 5.1–5.5
(all new compounds) were synthesized with the aim of estimating the
significance of the piperidine ring for the opioid analgesic activity of
anilido-piperidines. The starting b-keto-AMide 1.1,
prepared by the AMinolysis of methyl acetoacetate with methylphenethylAMine,
(93 % yield), was successively reacted with NaH and BuLi, to form the highly
reactive a,g-dienolate anion 1.1a. Regio and
chemoselective g-alkylation of the
dienolate with various primary and secondary alkyl halides furnished the b-keto-AMides 1.2–1.5 (76–91 %). Reductive AMination of the
keto-AMides 1.1–1.5 with aniline and Zn powder in acetic acid, via the
enAMine intermediates 2.1–2.5, afforded the b-anilino AMides 3.1–3.5 (74–85 %). After reductive
deoxygenation of the tertiary AMide group, using in situ generated diborane,
the corresponding 1,3-diAMines 4.1–4.5 were obtained (87–97 %). The
synthesis of (±)-2,3-seco-fentanyls 5.1–5.5 was completed by N-acylation
of the diAMines 4.1–4.5 with propionyl chloride, followed by
precipitation of the monooxalate salts (86–95 %). The parent compound, 2,3-seco-fentanyl
5.1, was found to be a 40 times less potent narcotic analgesic than fentanyl but
still 5–6 times more active than morphine in rats, while i-Pr derivative
5.3 was inactive. Apart from the pharmacological significance, the general
procedure described herein may afford various functionalized, 1,3-diAMines as
potential complexing agents and building blocks for the synthesis of aza-crown
ethers.
Keywords: open-chain fentanyl analogues, 1,3-diAMines, opioid analgesics.
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J. Serb. Chem.
Soc. 69 (11) 969–972 (2004) |
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Short communication
Antifungal activity of
davanone-type sesquiterpenes from Artemisia lobelii var. conescens
VLATKA VAJS, SNEZANA TRIFUNOVIC*, PEDJA
JANACKOVIC**, MARINA SOKOVIC***, SLOBODAN MILOSAVLJEVIC* and
VELE TESEVIC**
Institute for Chemistry,
Technology and Metallurgy, Njegoseva 12, 11001 Belgrade,
*Faculty of Chemistry, Studentski trg 16, P. O. Box 158, 11001 Belgrade,
**Faculty of Biology, Studentski trg 16, 11001 Belgrade and
***Institute for Biological Research “Sinisa Stankovic”, 29. Novembra 142,
11000 Belgrade, Serbia and Montenegro
(Received 25 June 2004)
Five tetrahydrofuran sesquiterpenes, so-called
davanones, and coumarin umbelliferone isolated from Artemisia lobelii All. var.
canescens (DC.) Briqu, were tested for antifungal activity. All the compounds
inhibited the growth of the applied fungi. The overall activity of one of them,
2-hydroxy-2,6,10-trimethyl-7,10-epoxydodeca- 3,11-dien-5-on, was comparable to
that of the antibiotic bifonazole.
Keywords: Artemisia lobelii All. var. conescens, Asteraceae, davanones,
umbelliferone, antifungal activity.
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J. Serb. Chem.
Soc. 69 (11) 973–980 (2004) |
To download this article click here 161 KB |
Effect of MnSOD (E.
coli) on the relaxation caused by sodium nitroprusside on isolated rat
renal artery
SLOBODAN R. MILOVANOVIC, ZORANA ORESCANIN*,
SNEZANA SPASIC**, SRDJAN MILETI**,
MILICA PROSTRAN*** and MIHAJLO B. SPASIC****
Military Medical
Academy, Crnotravska bb, 11000 Beolgrade,
*Institute for Medical Research, Dr. Subotica 4, 11000 Belgrade,
**Center for Chemistry, Institute of Chemistry, Technology and Metallurgy,
Njegoseva 12, 11000 Belgrade,
***Medical Faculty, University of Belgrade, Dr. Subotica 1, 11000 Belgrade and
****Institute for Biological Research “Sinisa Stankovic”, 29. Novembra 142,
11000 Belgrade, Serbia and Montenegro
(Received 20 May 2004)
In this study the molecular foundation of nitric
oxide induced relaxation of arteries, with or without endothelium, of
normotensive and spontanously hypertensive rats was re-exAMined. With this
purpose in mind, the effects of the nitric oxide donor sodium nitroprusside
(NaNP), with and without manganese containing superoxide dismutase (MnSOD E.C.
1.15.1.1.), on rat renal artery relaxation was strudied. The results show that
the relaxation effect of NaNP is two times higher in normotensive, compared to
spontaneously hypertensive rats. Similar differences exist in the relaxation
effects of NaNP on isolated renal arteries without endothelium, indicating that
besides the difference in the function of an endothelium, concerning basal NO
production in normotensive and hypertensive rats, there is a difference with
respect to NO relaxation in the smooth muscle that is induced by hypertension.
MnSOD decreased the relaxation effect of NaNP in all the exAMined renal
arteries, more in normotensive than in hypertensive ones regardless of the
presence of an endothelium. These results show that MnSOD, by modifying the
chemical versatility of NO into redox active forms - nitrosonium (NO+)
and nitroxyl (NO-), produces different relaxation effects in
normotensive and hypertensive arteries of rats, with or without an endothelium,
potentiating the role of nitroxyl induced relaxation in sponteneously
hypertensive rats. The results prove the need for the synthesis of complex NO
donors, as the mechanisms of artery relaxation are different due to an endothel
and smooth mouscle changes in hypertensive, as compared to normotensive rats.
Keywords: sodium nitroprusside, manganese superoxide dismutase, renal
artery, spontaneously hypertensive rats.
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J. Serb. Chem.
Soc. 69 (11) 981–990 (2004) |
To download this article click here 149 KB |
Stereoselective synthesis
of a-hydroxy-b-AMino acids: the chiral
pool approach
GORDANA TASIC, RADOMIR MATOVIC* and RADOMIR N.
SAICIC*,**
Faculty of Farmacy,
University of Belgrade, Vojvode Stepe 450, 11000 Belgrade,
*ICTM – Center for Chemistry, Njegoseva 12, 11000 Belgrade and
**Faculty of Chemistry, University of Belgrade, Studentski trg 16, P.O. Box
158, 11000 Belgrade, Serbia and Montenegro
(Received 15 April 2004)
A method for the stereoselective homologation of
a-AMino acids into syn-a-hydroxy-b-AMino acids is
described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines.
The synthetic potential of the method is illustrated in the enantioselective
formal synthesis of Bestatin.
Keywords: AMino acids, cyanohydrins, bestatin, AHPA, oxazoline.
Copyright &AMp; copy; SHD 2004.
December 22, 2004.
For
more information contact: JSCS@tmf.bg.ac.yu