Synthesis and antimicrobial activity of some new N-(aryloxoalkyl)-5- arylidene-thiazolidine-2,4-diones

Article abstract of DOI:10.2298/JSC130114078S

A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives (3a-h and 5a-h, respectively) were synthesized starting from 5-arylidenethiazolidine- -2,4-dione and α-halo-ketones. The struc

Full text of DOI:10.2298/JSC130114078S

J. Serb. Chem. Soc. 79 (2) 115–123 (2014)
UDC 547.53.024+547.78+547–316:615.281/.282
JSCS–4569
Original scientific paper
Synthesis and antimicrobial activity of some new
N-(aryloxoalkyl)-5-arylidene-thiazolidine-2,4-diones
1
1
2
3
*
ANCA STANA , BRÎNDUŞA TIPERCIUC , MIHAELA DUMA , ADRIAN PÎRNĂU ,
PHILIPPE VERITÉ4 and OVIDIU ONIGA1
1Department of Pharmaceutical Chemistry, “Iuliu Haţieganu” University of Medicine and
Pharmacy, 12 Ion Creangă Street, 400010 Cluj Napoca, Romania, 2State Veterinary
Laboratory for Animal Health and Food Safety, 400572 Cluj-Napoca, Romania, 3National
Institute for Research and Development of Isotopic and Molecular Technologies, 400293 Cluj
Napoca, Romania and 4University of Medicine and Pharmacy Rouen, Faculty of Pharmacy,
Department of Analytical Chemistry, 22 Boulevard Gambetta, F-76183 Rouen Cedex, France
(Received 13 January, revised 2 July 2013)
Abstract: A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione
and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives (3a–h and
5a–h, respectively) were synthesized starting from 5-arylidenethiazolidine-
-2,4-dione and α-halo-ketones. The structural elucidation of the newly syn-
thesized compounds was based on elemental analysis and spectroscopic data
1
(MS, H-NMR and 13C-NMR). The synthesized compounds were screened in
vitro for their antimicrobial activities against several pathogenic strains of
Gram-positive and Gram-negative bacteria and one fungal strain (Candida
albicans), as growth inhibition diameters. Some of the compounds displayed
better inhibitory activities than that of the reference drug against the Gram-
-positive Staphylococcus aureus, Bacillus cereus and Listeria monocytogenes
bacterial strains, and showed good antifungal activity against C. albicans,
while the antibacterial activity against the Gram-negative Escherichia coli and
Salmonella typhimurium bacterial strains was moderate.
Keywords: 5-arylidenethiazolidine-2,4-dione; α-haloketone; antibacterial; anti-
fungal.
INTRODUCTION
Heterocyclic compounds have long been recognized in the field of synthetic
organic chemistry as a very important class. Nitrogen-, oxygen- and sulphur-
-containing heterocyclic compounds are known to exhibit a large variety of bio-
1
logical activities and are used in various fields of pharmacy.
*Corresponding author. E-mail: teodora_anca@yahoo.com
doi: 10.2298/JSC130114078S
115
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STANA et al.
Especially great attention has been given to thiazolidine-2,4-dione deri-
vatives as they posses a diverse array of pharmacological activities, such as
2
3
4
antidiabetic, antioxidant, analgesic, anti-arthritic, anti-inflammatory, antican-
5
6
cer, antibacterial and antifungal. Besides showing a remarkable antidiabetic
activity by binding with PPARγ, heterocyclic compounds bearing thiazolidine-
-2,4-dione moiety with substitution at the fifth position can reduce oxidative
7
stress and inhibit intracellular free radical overproduction. They also have inhi-
bitory effects on monocyte/macrophage activation, the expression of inflamma-
8
9
tory molecules and tyrosinase activity. It was reported that 5-arylidene-2,4-
-thiazolidinediones can act as potentially promising 15-hydroxyprostaglandin
10
11
dehydrogenase inhibitors,
inhibitors of MurD ligase
and antimicrobial
12–14
agents.
The search for new high-effective antimicrobial drugs is a very important
issue because of the appearance of a large group of antibiotic and antifungal
15
resistant strains.
In view of these facts and in continuation of efforts to discover potentially
16
active new antimicrobial agents, the synthesis of two series of various N-sub-
stituted 5-arylidene-thiazolidine-2,4-diones and an evaluation of their antibac-
terial and antifungal activities are reported herein.
RESULTS AND DISCUSSION
Chemistry
The synthetic strategy for the target compounds, N-(aryloxoalkyl)-5-(2,6-
-dichlorobenzylidene)thiazolidine-2,4-diones (3a–h) and N-(aryloxoalkyl)-5-(4-
-methoxybenzylidene)thiazolidine-2,4-diones (5a–h) is illustrated in Scheme 1.
The general method known as the Knoevenagel condensation was used to
synthesize the N-unsubstituted 5-arylidene-thiazolidine-2,4-diones (2 and 4) in
good yields (94–95 %). 5-(2,6-Dichlorobenzylidene)thiazolidine-2,4-dione (2)
and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione (4) were prepared by the
condensation of thiazolidine-2,4-dione with the appropriate arylaldehyde, accord-
17,18
ing to procedures reported in the literature.
In order to accomplish N-substitution, the 5-arylidenethiazolidine-2,4-diones
(2 and 4) were first converted into potassium salts at the nitrogen atom of the
thiazolidine-2,4-dione ring with the help of anhydrous potassium hydroxide in
dimethylformamide (DMF) under continuous stirring at room temperature. The
treatment of the obtained potassium salts with various α-halo-ketones in DMF
under continuous stirring at room temperature afforded the target compounds, N-
(aryloxoalkyl)-5-arylidene-thiazolidine-2,4-diones (3a–h and 5a–h, respectively)
in 45–95 % yields.
The newly synthesized N-substituted 5-arylidenethiazolidine-2,4-diones (3a–h
and 5a–h) were characterized by melting point, elemental analysis and spectro-
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1
13
scopic data ( H-NMR, C-NMR and MS). All compounds gave good CHNS
quantitative elemental analysis results, in agreement with the calculated values.
All spectral and analytical data were consistent with the assumed structures.
Details of the synthetic procedures and the yields are presented in the Experi-
mental while the physical, analytical and spectral data for the synthesized com-
pounds are given in the Supplementary material to this paper.
Scheme 1. General synthetic route for the synthesis of the compounds 3a–h and 5a–h.
The IR spectra of the synthesized compounds 3a–h and 5a–h displayed three
–1
–1
strong absorption peaks at 1749–1731 cm , 1705–1692 cm and 1687–1668
–1
cm due to C=O stretching of the thiazolidine-2,4-dione ring and the arylalkyl-
ketone, respectively. The absence of absorption bands corresponding to the
–NO group of the thiazolidine-2,4-dione moiety in the IR spectra of all the newly
synthesized compounds confirmed the formation of N-substituted derivatives.
–1
Compounds 3b and 5a–h give two strong bands at 1043–1031 cm and 1258–
–1
–1248 cm due to the presence of phenyl methyl ether group. The absorption
–1
–1
bands at 1521–1517 cm and 1331–1324 cm in the IR spectra of compounds
3c and 5c are due to the asymmetric and symmetric stretch of the –NO group.
2
The IR spectra of compounds 3e and 5e exhibited one sharp absorption at 2235–
–1
–2231 cm due to the –C≡N stretch. In the IR spectra of compounds 3f and 5f,
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STANA et al.
–1
the C=O stretch of the amide group appeared at 1635–1628 cm and the phenol
–1
group presented an absorption band at 1233–1231 cm due to the C–O stretch-
–1
ing vibration and an absorption band at 3417–3411 cm due to the intramole-
cular hydrogen-bonded OH stretch.
1
The H-NMR spectra of the synthesized compounds 3a–h and 5a–h showed
one signal for the methylidene proton, as a singlet at 7.879–7.991 ppm, which
supported the occurrence of the Knoevenagel condensation between the thiazoli-
dine-2,4-dione and aromatic aldehydes. The absence of a singlet signal corres-
ponding to the NH proton from the thiazolidine-2,4-dione ring in the 12.50–12.52
16
1
ppm region in the H-NMR spectra of all compounds confirmed the formation
of N-substituted derivatives. The –OCH protons resonated as singlets at 3.822–
3
–3.896 ppm and the aromatic protons appeared as characteristic doublets, triplets
1
13
or multiplets in the 7.043–8.902 ppm region of the H-NMR spectra. C-NMR
spectra of the synthesized compounds were in accordance with the assumed
structures.
The mass spectra of the synthesized compounds gave idea about the frag-
mentation of the final compounds with their corresponding mass and revealed the
+
correct molecular ion peaks (M or M+1), as suggested by their molecular
formulas.
Antibacterial/antifungal activity
All compounds were tested for their antibacterial activity against two Gram-
-negative (Salmonella typhimurium ATCC 13311 and Escherichia coli ATCC
25922) and three Gram-positive (Listeria monocytogenes ATCC 35152, Sta-
phylococcus aureus ATCC 25923 and Bacillus cereus ATCC 13061) bacterial
strains. The antifungal activity of the compounds was evaluated against a strain
of Candida albicans ATCC 90028.
The results of the antifungal and antibacterial activity of the N-(aryloxo-
alkyl)-5-arylidenethiazolidine-2,4-diones 3a–h and 5a–h in comparison with those
of reference drugs are presented in Table I.
All the tested compounds presented modest to good inhibitory activity
against the Gram-positive and the Gram-negative bacteria, compared to cipro-
–1
floxacin (50 μg well ), employed as a standard drug. All of the synthesized
compounds were active and showed moderate activity against E. coli and S.
typhimurium (10–18 mm inhibition zone). The 5-(4-methoxybenzylidene)thiazo-
lidine-2,4-diones (5a–h) were generally more active than the 5-(2,6-dichloroben-
zylidene)thiazolidine-2,4-diones (3a–h), suggesting that substitution of the thia-
zolidine-2,4-dione ring with a methoxybenzylidene moiety in the fifth position
rather than with a 2,6-dichlorobenzylidene moiety favoured the antibacterial
activity of the compounds against Gram-negative bacteria. On the contrary, the
5-(2,6-dichlorobenzylidene)thiazolidine-2,4-diones 3a–h exhibited better anti
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-bacterial properties than the 5-(4-methoxybenzylidene)thiazolidine-2,4-diones
(5a–h) did against the Gram-positive bacteria. Compounds 3a,c,e and f and 5a–c
displayed similar or better inhibitory activities than that of the reference drug
ciprofloxacin against S. aureus, while compounds 3e–f were more active than
ciprofloxacine against L. monocytogenes, and compound 3f was more active than
the standard against B. cereus. The antibacterial activity of compounds 3a, 3c
and 3e–f and 5a–c was generally better than that of the other N-(aryloxoalkyl)-
-5-arylidenethiazolidine-2,4-diones, suggesting that the presence of an electron
withdrawing group, such as nitro, nitrile or carbonyl, on the aromatic ring plays
an important role in enhancing the antibacterial properties of the titled com-
pounds. Regarding the antifungal activity, most of the synthesized compounds
showed moderate to good inhibition (14–24 mm inhibition zone) against C. albi-
cans, at the test concentrations.
TABLE I. Antimicrobial activity of the synthesized compounds 3a–h and 5a–h; inhibition
zone, mm; (–) no activity
Gram-positive bacteria
S. aureus L. monocytogenes B. cereus E. coli S. typhimurium C. albicans
Gram-negative bacteria
Fungi
Compound
3a
3b
3c
3d
3e
3f
3g
3h
5a
5b
5c
5d
5e
5f
5g
5h
20
18
28
18
22
20
18
18
20
20
24
18
18
18
18
18
20
–
18
16
16
16
28
22
18
16
18
18
16
16
18
18
16
16
22
–
20
12
18
16
20
24
16
14
14
14
12
12
12
14
12
12
22
–
16
12
14
12
12
10
10
10
14
14
12
12
14
14
18
16
24
–
14
12
16
14
12
16
14
14
18
18
18
18
16
18
18
18
22
–
14
18
16
18
22
22
24
18
18
18
16
16
14
14
16
16
–
Ciprofloxacina
Fluconazolea
25
a
-1
Ciprofloxacin and fluconazole (50 μg well ) were used as standard drugs
EXPERIMENTAL
Chemistry
All chemicals and reagents were obtained from commercial sources and were used as
supplied, without further purification. Compounds 2 and 4 were previously reported in the
literature.16-18
Melting points were determined with an electrothermal melting point meter in open glass
capillary method and are uncorrected. The reaction progress and purity of the synthesized
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compounds were monitored by analytical thin layer chromatography (TLC) using Merck pre-
coated Silica Gel 60F254 sheets (Darmstadt, Germany), a heptane–ethyl acetate 3:7 elution
system and UV light for visualization. The IR spectra were recorded on a JASCO FT-IR-4100
spectrometer (Cremella, Italy) using the ATR technique (Attenuated Total Reflectance). The
nuclear magnetic resonance (1H-NMR) spectra were recorded at room temperature on Bruker
Avance NMR spectrometer (Karlsruhe, Germany) operating at 500 and 125 MHz for 1H- and
13C-NMR, respectively, using tetramethylsilane (TMS) as an internal standard (chemical
shifts, δ, in ppm). The spectra were in accordance with the assigned structures. The samples
were prepared by dissolving the compounds in DMSO-d6 (δH = 2.51 ppm) as solvent and the
spectra were recorded using a single excitation pulse of 12 μs (1H-NMR). Spin multiplets are
given as s (singlet), d (doublet), t (triplet) and m (multiplet). The 13C-NMR spectra were
recorded on a Bruker Avance NMR spectrometer (Karlsruhe, Germany) operating at 125 MHz
in DMSO-d6, using a waltz-16 decoupling scheme. The MS analyses were performed at 70 eV
with an Agilent gas chromatograph 6890 (Darmstadt, Germany) equipped with an apolar
Macherey Nagel Permabond SE 52 capillary column (Dueren, Germany) and with an LCMS-
-2020 Shimadzu mass spectrometer (Shimadzu Corporation, North America). Elemental
analyses were realized using a Vario El CHNS instrument (Hanau, Germany). Physical,
analytical and spectral data of the prepared compounds are given in Supplementary material to
this paper.
5-(2,6-Dichlorobenzylidene)-3-(2-oxo-2-phenylethyl)thiazolidine-2,4-dione (3a). 1 mmol
(273 mg) of 2 was dissolved in dimethylformamide (DMF) (3.5 mL) and finely dispersed
anhydrous potassium hydroxide (84 mg, 1.5 mmol) was added. The mixture was stirred for 30
min at room temperature to give the potassium salt of 5-(2,6-dichlorobenzylidene)thiazo-
lidine-2,4-dione. To the resulting suspension was added 2-bromo-1-phenylethanone (199 mg,
1 mmol) for N-substitution. The mixture was stirred at room temperature for 8 h. The reaction
was monitored by TLC. After completion of the reaction, the reaction mass was poured into
ice-cold water. The resulting precipitate was filtered, washed with water and ethanol, dried
and then recrystallized from absolute ethanol. Yellow solid; yield: 85 %.
5-(2,6-Dichlorobenzylidene)-3-[2-(4-methoxyphenyl)-2-oxoethyl]thiazolidine-2,4-dione
(3b). Using 2-bromo-1-(4-methoxyphenyl)ethanone (229 mg, 1 mmol), the compound was
prepared according to the procedure described for 3a. White solid; yield: 93 %.
5-(2,6-Dichlorobenzylidene)-3-[2-(4-nitrophenyl)-2-oxoethyl]thiazolidine-2,4-dione
(3c). The compound was prepared according to the procedure for 3a using 2-bromo-1-(4-
-nitrophenyl)ethanone (244 mg, 1 mmol). Dark brown solid; yield: 69 %.
3-[2-(4-Chlorophenyl)-2-oxoethyl]-5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione (3d).
The title compound was prepared according to the procedure described for 3a using 2-bromo-
-1-(4-chlorophenyl)ethanone (233.5 mg, 1 mmol). Brown solid; yield: 74 %.
4-{2-[5-(2,6-Dichlorobenzylidene)-2,4-dioxothiazolidin-3-yl]acetyl}benzonitrile (3e). The
title compound was prepared following the procedure presented for 3a using 4-(2-bromo-
acetyl)benzonitrile (224 mg, 1 mmol) and was recrystallized from absolute ethanol. Yellow
solid; yield: 51 %.
5-{2-[5-(2,6-Dichlorobenzylidene)-2,4-dioxothiazolidin-3-yl]acetyl}-2-hydroxybenzamide
(3f). The compound was prepared using 5-(2-bromoacetyl)-2-hydroxybenzamide (258 mg, 1
mmol) following the synthetic procedure described for 3a. Brown solid; yield: 53 %.
5-(2,6-Dichlorobenzylidene)-3-(1-methyl-2-oxo-2-phenylethyl)thiazolidine-2,4-dione
(3g). The title compound was prepared following the procedure presented for 3a using
2-bromo-1-phenylpropan-1-one (213 mg, 1 mmol). Yellow liquid; yield: 45 %.
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5-(2,6-Dichlorobenzylidene)-3-[2-(naphthalen-2-yl)-2-oxoethyl]thiazolidine-2,4-dione
(3h). The title compound was prepared using 2-bromo-1-(naphthalen-2-yl)ethanone (249 mg,
1 mmol) according to the procedure described for 3a. White solid; yield: 78 %.
5-(4-Methoxybenzylidene)-3-(2-oxo-2-phenylethyl)thiazolidine-2,4-dione (5a). To a solu-
tion of 4 (235 mg, 1 mmol) in DMF (3.5 mL) was added finely dispersed anhydrous
potassium hydroxide (84 mg, 1.5 mmol). The mixture was stirred for 30 min at room tempe-
rature to give the potassium salt of 5-(4-methoxybenzylidene)thiazolidine-2,4-dione. To the
resulting suspension was added 2-bromo-1-phenylethanone (199 mg, 1 mmol) and then the
reaction mixture was stirred at room temperature for 8 h. TLC was used to monitor the reac-
tion progress. After completion of the reaction, the mass was poured into ice-cold water under
continuous stirring. The resulting compound was washed with water and ethanol, dried and
then recrystallized from absolute ethanol. White solid; yield: 79 %.
5-(4-Methoxybenzylidene)-3-(2-(4-methoxyphenyl)-2-oxoethyl)thiazolidine-2,4-dione (5b).
Using 2-bromo-1-(4-methoxyphenyl)ethanone (229 mg, 1 mmol), the title compound was
prepared according to the procedure described for 5a. White solid; yield: 95 %.
5-(4-Methoxybenzylidene)-3-[2-(4-nitrophenyl)-2-oxoethyl]thiazolidine-2,4-dione (5c). The
title compound was prepared according to the procedure for 5a but using 2-bromo-1-(4-
-nitrophenyl)ethanone (244 mg, 1 mmol). Pale yellow solid; yield: 92 %.
3-[2-(4-Chlorophenyl)-2-oxoethyl]-5-(4-methoxybenzylidene)thiazolidine-2,4-dione (5d).
The title compound was prepared according to the procedure described for 5a but using
2-bromo-1-(4-chlorophenyl)ethanone (233.5 mg, 1 mmol). White solid; yield: 78 %.
4-{2-[5-(4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetyl}benzonitrile (5e). Fol-
lowing the procedure presented for 5a, the title compound was prepared using 4-(2-bromo-
acetyl)benzonitrile (224 mg, 1 mmol) and was recrystallized from absolute ethanol. Light
brown solid; yield: 53 %;
2-Hydroxy-5-{2-[5-(4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl]acetyl}benzamide
(5f). The compound was prepared using 5-(2-bromoacetyl)-2-hydroxybenzamide (258 mg, 1
mmol) according to the synthetic procedure described for 5a. Yellow solid; yield: 62 %.
5-(4-Methoxybenzylidene)-3-(1-methyl-2-oxo-2-phenylethyl)thiazolidine-2,4-dione (5g).
Following the procedure presented for 5a but using 2-bromo-1-phenylpropan-1-one (213 mg,
1 mmol), the title compound was prepared. White solid; yield: 64 %.
5-(4-Methoxybenzylidene)-3-[2-(naphthalen-2-yl)-2-oxoethyl]thiazolidine-2,4-dione (5h).
The title compound was prepared using 2-bromo-1-(naphthalen-2-yl)ethanone (249 mg, 1
mmol) according to the procedure described for 5a. White solid; yield: 81 %.
Antibacterial/antifungal activity
The in vitro antimicrobial activity was determined using the cup-plate agar diffusion
method according to the Clinical and Laboratory Standards Institute (CLSI) guidelines.19
For antibacterial testing, Mueller–Hinton agar medium was used whereas for antifungal
testing, Mueller–Hinton medium supplemented with 2 % glucose (providing adequate growth
of yeasts) and 0.5 mg mL-1 methylene blue (providing a better definition of the inhibition zone
diameter) was used. The inoculum was prepared by suspending five representative colonies,
obtained from an 18–24 h culture on non-selective nutritive agar medium, in sterile distilled
water. The cell density was adjusted to the density of 0.5 McFarland standard by measuring
the absorbance in a spectrophotometer at a wavelength of 530 nm and adding sterile distilled
water as required (corresponding to a population of (1–5)×106 CFU mL-1). A sterile swab was
soaked in suspension and then the Mueller–Hinton agar plates were inoculated by streaking
the entire surface. After drying for 10–15 min, six mm-diameter wells were cut from the agar
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using a sterile cork-borer, and a volume of 10 μL of each compound solution (5 mg mL-1 in
DMSO) were delivered into the wells (50µg well-1). Ciprofloxacin (50 μg well-1) and
fluconazole (50 μg well-1) were used as standard drugs. The controls were performed with
only sterile broth, overnight culture and 10 μL DMSO. The plates were incubated at 35 °C.
The inhibition zone diameters were measured to the nearest whole millimetre where there was
no visible growth after 24–48 h. The results were obtained in triplicate. The solvent used for
the preparation of each compound stock solution (5 mg ml-1), DMSO (Merck, Germany)
exhibited no inhibitory activity against the tested bacterial and fungal strains.
CONCLUSIONS
In conclusion, a series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-
-dione and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives were
synthesized by Knoevenagel condensation of thiazolidine-2,4-dione with the
required aromatic aldehyde, followed by N -substitution with various α-halo-
3
1
-ketones. Their structures were confirmed by analytical techniques: H-NMR,
C-NMR, mass and elemental analysis. The synthesized compounds were
13
evaluated for their antibacterial and antifungal activities against several Gram-
positive, Gram-negative bacteria and Candida albicans. The results of the anti-
microbial screening revealed that all of the tested compounds have antibacterial
and antifungal properties, while some showed promising antimicrobial activities:
compounds 3c, 3e and 5c displayed better inhibitory activities than ciprofloxacin
against S. aureus, compounds 3e and 3f were more active against L. mono-
cytogenes and compound 3f was more active against B. cereus than ciproflox-
acin.
SUPPLEMENTARY MATERIAL
Physical, analytical and spectral data of the prepared compounds are available electro-
nically from http://www.shd.org.rs/JSCS/, or from the corresponding author on request.
И З В О Д
СИНТЕЗА И АНТИМИКРОБНА АКТИВНОСТ НОВИХ N-(АРИЛОКСОАЛКИЛ)-5-
-АРИЛИДЕНТИАЗОЛИДИН-2,4-ДИОНА
ANCA STANA1, BRÎNDUŞA TIPERCIUC1, MIHAELA DUMA2, ADRIAN PÎRNĂU3, PHILIPPE VERITÉ4
и OVIDIU ONIGA1
1
Department of Pharmaceutical Chemistry,“Iuliu Haţieganu” University of Medicine and Pharmacy, 12 Ion
2
Creangă Street, 400010 Cluj Napoca, Romania, State Veterinary Laboratory for Animal Health and Food
3
Safety, 400572 Cluj-Napoca, Romania, National Institute for Research and Development of Isotopic and
4
Molecular Technologies, 400293 Cluj Napoca, Romania и University of Medicine and Pharmacy Rouen,
Faculty of Pharmacy, Department of Analytical Chemistry, 22 Boulevard Gambetta, F-76183 Rouen Cedex,
France
Синтетисана је серија нових деривата 5-(2,6-дихлоробензилиден)тиазолидин-2,4-
-диона и 5-(4-метоксибензилиден)тиазолидин-2,4-дионa (3a–h и 5a–h) полазећи од
5-арилидентиазолидин-2,4-диона и α-халоген-кетона. Структура нових једињења одре-
1
ђена је на основу елементалне анализе и спектроскопских података (IR, MS, H-NMR и
13C-NMR). Одређена је антимикробна активност синтетисаних једињења према неко-
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лико сојева грам-позитивних и грам-негативних бактерија и соју гљивица (Candida albi-
cans). Нека од синтетисаних једињења показују добру активност према C. albicans, док је
активност према сојевима грам-негативних бактерија Escherichia coli и Salmonella typhi-
murium умерена.
(Примљено 13. јануара, ревидирано 2. јула 2013)
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