Synthesis and antimicrobial activities of some 1-[(N,N- disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines

Article abstract of DOI:10.1080/104265090930452

The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this purpose, new pyrazoline derivatives were synthesized and evaluated for antimicrobial activity. Some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines derivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2- pyrazolines with appropriate potassium salts of secondary amine dithiocarbamic acids. The chemical structures of the compounds were elucidated by IR, ¹H-NMR, and FAB⁺-MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida albicans (NRRL-27077) were investigated. The results showed that some of the compounds have notable activity against S. aureus and C. albicans. Copyright Taylor & Francis Inc.

Full text of DOI:10.1080/104265090930452

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Synthesis and Antimicrobial
Activities of Some 1-[(N, N-
Disubstitutedthiocarbamoylthio)ace
diaryl-2-pyrazolines
Gülhan Turan-Zitouni a , Ahmet Özdemir a , Zafer
Asim Kaplancikli a , Pierre Chevallet b & Yagmur
Tunali c
a Department of Pharmaceutical Chemistry, Anadolu
University, Faculty of Pharmacy, Eskişehir, Turkey
b Department of Pharmaceutical Chemistry,
Montpellier University, LAAP, Montpellier, France
c Department of Microbiology, Anadolu University,
Faculty of Pharmacy, Eskişehir, Turkey
Published online: 19 Aug 2006.
To cite this article: Glhan Turan-Zitouni , Ahmet zdemir , Zafer Asim Kaplancikli ,
Pierre Chevallet & Yagmur Tunali (2005) Synthesis and Antimicrobial Activities of
Some 1-[(N, N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines,
Phosphorus, Sulfur, and Silicon and the Related Elements, 180:12, 2717-2724, DOI:
10.1080/104265090930452
To link to this article: http://dx.doi.org/10.1080/104265090930452
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Phosphorus, Sulfur, and Silicon, 180:2717–2724, 2005
Copyright © Taylor & Francis Inc.
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/104265090930452
Synthesis and Antimicrobial Activities of Some
1-[(N,N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-
diaryl-2-pyrazolines
¨
Gulhan Turan-Zitouni
¨
Ahmet Ozdemir
Zafer Asım Kaplancikli
Anadolu University, Faculty of Pharmacy, Department of
Pharmaceutical Chemistry, Eskis¸ehir, Turkey
Pierre Chevallet
Montpellier University, Department of Pharmaceutical Chemistry,
LAAP, Montpellier, France
Yagmur Tunali
Anadolu University, Faculty of Pharmacy, Department of Microbiology,
Eskis¸ehir, Turkey
The increasing clinical importance of drug-resistant fungal and bacterial pathogens
has lent additional urgency to microbiological research and new antimicrobial com-
pound development. For this purpose, new pyrazoline derivatives were synthesized
and evaluated for antimicrobial activity.
Some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines de-
rivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines
with appropriate potassium salts of secondary amine dithiocarbamic acids. The
chemical structures of the compounds were elucidated by IR, 1 H-NMR, and FAB+-
MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-
767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus
vulgaris (NRLL B-123), and Candida albicans (NRRL-27077) were investigated.
The results showed that some of the compounds have notable activity against S.
aureus and C. albicans.
Keywords Antimicrobial activity; dithiocarbamic acid; pyrazoline
INTRODUCTION
Pyrazoline derivatives constitute an interesting class of organic com-
pounds with diverse chemical1 and pharmacological applications.
Received November 2, 2004; in final form December 30, 2004.
Address correspondence to Gu¨lhan Turan-Zitouni, Anadolu University, Faculty of
Pharmacy, Department of Pharmaceutical Chemistry, Eskis¸ehir 26470, Turkey. E-mail:
gturan@anadolu.edu.tr
2717

2718
G. Turan-Zitouni et al.
The potential activity of 2-pyrazolines as antibacterial,2−3 anti-
fungal,4,5 anti-inflammatory, analgesic,6,7 antidepressant,8,9 and anti-
convulsant10 agents are well known.
It is also well known that N-mono and N,N-disubstituted dithiocarba-
mate derivatives show antibacterial and antifungal activities.11,12 The
structure–activity relationship study revealed that the antibacterial
activity of thiocarbonyl aromatic compounds was significantly affected
by the lipophilicity which is obtained by the thiocarbonyl moiety.13,14
Keeping these observations in mind, we decided to undertake
the synthesis of 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3,5-
diaryl-2-pyrazolines carrying an N,N-disubstituted dithiocarbamate
moiety and to study their antimicrobial activity.
RESULTS AND DISCUSSION
Chemistry
In the present work, 16 new compounds were synthesized. The
reaction of 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines (5) with appro-
priate potassium salts of secondary amine dithiocarbamic acids
(6) gave 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-
pyrazolines (7) (Scheme 1, Table I).
SCHEME 1

Synthesis and Antimicrobial Activities
2719
TABLE I Some Characteristics of the Compounds
M.P. Yield
(◦C) (%)
Molecular
formula
Compound
R1
R2
R3
5a
5b
5c
5d
7a
7b
7c
7d
7e
7f
7g
7h
7i
7j
7k
7l
Phenyl
Phenyl
3,4-CH3-phenyl
Tetrahydronaphtalene
Phenyl
Phenyl
Phenyl
Phenyl
Phenyl
H
OCH3
H
H
H
H
H
H
—
—
—
133 70 C17H15ClN2O
129 73 C18H17ClN2O2
112 79 C19H19ClN2O
109 77 C21H21ClN2O
—
Piperidine
Pyrrolidine
Morpholine
122 85
C23H25N3OS2
156 84 C22H23N3OS2
158 83 C22H23N3O2S2
Thiomorpholine 188 81 C22H23N3OS3
OCH3 Piperidine
OCH3 Pyrrolidine
OCH3 Morpholine
148 85 C24H27N3O2S2
159 85 C23H25N3O2S2
163 82 C23H25N3O3S2
Phenyl
Phenyl
Phenyl
OCH3 Thiomorpholine 142 80 C23H25N3O2S3
3,4-CH3-phenyl
3,4-CH3-phenyl
3,4-CH3-phenyl
3,4-CH3-phenyl
Tetrahydronaphtalene
Tetrahydronaphtalene
Tetrahydronaphtalene
Tetrahydronaphtalene
H
H
H
H
H
H
H
H
Piperidine
Pyrrolidine
Morpholine
134 85 C25H29N3OS2
177 84 C24H27N3OS2
167 85 C24H27N3O2S2
Thiomorpholine 150 82 C24H27N3OS3
7m
7n
7o
7p
Piperidine
Pyrrolidine
Morpholine
118 76 C27H31N3OS2
142 73 C26H29N3OS2
148 78 C26H29N3O2S2
Thiomorpholine 174 81 C26H29N3OS3
IR (KBr, cm−1): These Compounds Showed Characteristic IR Bands at
1670–1675 cm−1 (C O), 1225–1255 cm−1 (C S), 1575–1590 (C N), and 1530–1550
(C C).
IR data were very informative. In the IR spectra, some significant
stretching bands due to C O, C N, C C and C S were at 1670–
1675 cm−1, 1575–1590 cm−1, 1530–1550 cm−1, and 1225–1255 cm−1
,
respectively.
1
In the H-NMR spectra HA, HB, and HX protons of the pyrazoline
ring were seen as a doublet of doublets at about 3.10–3.20 ppm, 3.80–
3.90 ppm, and 5.50–5.60 ppm, respectively. COCH2 methylene protons,
present in all compounds, appeared at 4.60–4.80 ppm as two doublets.
All the other aromatic and aliphatic protons were observed at the ex-
pected regions.
Mass spectra (MS (FAB)) of the compounds showed a M+1 peaks, in
agreement with their molecular formula (Table II).
Microbiology
All compounds were evaluated for their antimicrobial properties. Con-
siderable activity was observed against S. aureus. In comparison with

2720
G. Turan-Zitouni et al.
TABLE II Selected 1H-NMR (δ ppm) (DMSO d6) and MS (FAB+) m/z of
the Compounds
Compound
1H-NMR
MS
5a
4.65 (1H, d (J = 13.84 Hz), CH2-Cl), 4.80 (1H, d (J = 13.83 Hz), 299 [M+1]
CH2-Cl)
5c
5d
7a
4.60 (1H, d (J = 13.84 Hz), CH2-Cl), 4.75 (1H, d (J = 13.84 Hz), 327 [M+1]
CH2-Cl)
4.65 (1H, d (J = 13.84 Hz), CH2-Cl), 4.70 (1H, d (J = 13.84 Hz), 353 [M+1]
CH2-Cl)
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.60 (1H, d (J = 424 [M+1]
16.03 Hz), CH2-S), 4.80 (1H, d (J = 16.04 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.25 Hz, JAX = 4.76 Hz,
JBX = 11.70 Hz)
7b
7c
7d
7f
3.10–3.20 (1H, dd, HA), 3.85–4.00 (1H, dd, HB), 4.60 (1H, d (J =
17.78 Hz), CH2-S), 4.80 (1H, d (J = 17.74 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.25 Hz, JAX = 4.76 Hz,
JBX = 11.70 Hz)
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.60 (1H, d (J =
16.05 Hz), CH2-S), 4.80 (1H, d (J = 16.06 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.07 Hz, JAX = 4.70 Hz,
JBX = 11.63 Hz)
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.60 (1H, d (J = 442 [M+1]
16.11 Hz), CH2-S), 4.80 (1H, d (J = 16.10 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.00 Hz, JAX = 4.65 Hz,
JBX = 11.78 Hz)
3.10–3.20 (1H, dd, HA), 3.90–4.00 (1H, dd, HB), 4.60 (1H, d (J = 440 [M+1]
15.99 Hz), CH2-S), 4.80 (1H, d (J = 15.97 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.12 Hz, JAX = 4.55 Hz,
JBX = 11.77 Hz)
7h
7i
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.60 (1H, d (J = 472 [M+1]
16.03 Hz), CH2-S), 4.80 (1H, d (J = 16.03 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 17.60 Hz, JAX = 4.60 Hz,
JBX = 11.70 Hz)
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.70 (1H, d (J =
17.80 Hz), CH2-S), 4.80 (1H, d (J = 17.80 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 17.88 Hz, JAX = 4.66 Hz,
JBX = 11.70 Hz)
7k
7l
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.70 (1H, d (J =
17.85 Hz), CH2-S), 4.80 (1H, d (J = 17.83 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 17.89 Hz, JAX = 4.70 Hz,
JBX = 11.65 Hz)
3.10–3.20 (1H, dd, HA), 3.80–4.00 (1H, dd, HB), 4.60 (1H, d (J = 470 [M+1]
16.11 Hz), CH2-S), 4.80 (1H, d (J = 16.15 Hz), CH2-S),
5.50-5.60 (1H, dd, HX),. (JAB = 18.09 Hz, JAX = 4.62 Hz,
JBX = 11.60 Hz)
7m
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.70 (1H, d (J = 478 [M+1]
16.07 Hz), CH2-S), 4.80 (1H, d (J = 16.04 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 18.02 Hz, JAX = 4.47 Hz,
JBX = 11.55 Hz)

Synthesis and Antimicrobial Activities
2721
TABLE II Selected 1H-NMR (δ ppm) (DMSO d6) and MS (FAB+) m/z of
the Compounds (Continued)
Compound
1H-NMR
MS
7o
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.70 (1H, (d J = 480 [M+1]
16.11 Hz), CH2-S), 4.80 (1H, d (J = 16.11 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 17.89 Hz, JAX = 4.43 Hz,
JBX = 11.52 Hz)
7p
3.10–3.20 (1H, dd, HA), 3.80–3.90 (1H, dd, HB), 4.70 (1H, d (J = 496 [M+1]
16.09 Hz), CH2-S), 4.80 (1H, d (J = 16.08 Hz), CH2-S),
5.50–5.60 (1H, dd, HX), (JAB = 17.80 Hz, JAX = 4.56 Hz,
JBX = 11.73 Hz)
the control antibacterial agent chloramphenicole, an important antibac-
terial activity was observed for compound 5d (1.56 µg/mL) against S.
aureus. Moreover, 7a, 7e, and 7g (6.25 µg/mL) also showed significant
activity against S. aureus. The other compounds showed approximately
similar MIC values against S. aureus when compared with the control
compound.
On the other hand, the compounds 7b, 7e, 7f, and 7n exhibited sig-
nificant antifungal activity against C. albicans, whereas the other com-
pounds showed similar activity when compared with the control value.
In comparison with the reference, agent all of the compounds showed
similar activity against P. aeuroginosa. Only the compounds 7d and 7k
showed the same activity against P. vulgaris, whereas all other com-
pounds showed moderate activities when compared with chlorampheni-
cole (Table III).
EXPERIMENTAL
Chemistry
Melting points were determined by using a Gallenkamp apparatus and
were uncorrected. Spectroscopic data were recorded by the following
1
instruments: IR, Shimadzu 435 spectrophotometer; H-NMR. Bruker
250 MHz spectrometer; and MS, VG Quattro mass spectrometer.
General Synthetic Procedure 1,3-Diaryl-2-propen-1-ones (3)
1,3-diaryl-2-propen-1-one derivatives were synthesized by condensing
the appropriate acetophenones (1) with substituted benzaldehydes (2)
according to the Claisen-Schmidt condensation.15

2722
G. Turan-Zitouni et al.
TABLE III Antimicrobial Activities of the Compounds as MIC Values
(µg/mL). Control Compounds: A; Ketoconazole; B; Chloramphenicole
Compound
S. aureus
P. aeruginosa
P. vulgaris
E. coli
C. albicans
5a
5b
5c
5d
7a
7b
7c
7d
7e
7f
7g
7h
7i
7j
7k
7l
12.5
12.5
12.5
1.56
6.25
12.5
12.5
12.5
6.25
12.5
6.25
12.5
12.5
12.5
12.5
12.5
12.5
12.5
12.5
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
—
50
50
50
50
50
50
50
25
50
50
50
50
50
50
25
50
50
50
50
50
—
25
25
25
25
25
25
25
25
25
25
50
25
25
25
25
25
25
25
25
25
—
50
50
50
50
50
25
50
50
25
25
50
50
50
50
50
50
50
25
50
50
50
—
7m
7n
7o
7p
A
—
12.5
B
25
25
12.5
3,5-Diaryl-2-pyrazolines (4)
To the solution of 0.02 mol of the appropriate 1,3-diaryl-2-propen-1-ones
(3) derivative in 20 mL of ethanol, 0.04 mol of hydrazine hydrate was
added and the reaction mixture was refluxed for 4 h. The reaction mix-
ture was cooled at 0◦C overnight and the precipitate was then filtered
and washed with ethanol.1
1-(Chloroacetyl)-3,5-diaryl-2-pyrazolines (5)
The 3,5-diaryl-2-pyrazolines (4) (0.015 mol) and triethylamine
(0.015 mol) were dissolved in dry benzene (30 mL) with constant stir-
ring. Then the mixture was cooled in an ice bath, and chloroacetylchlo-
ride (0.015 mol) was added dropwise with stirring. The reaction mixture
was agitated for 1 h at r.t. The precipitate was filtered. The filtrate was
evaporated to dryness under reduced pressure and the products were
recrystallized from ethanol.16

Synthesis and Antimicrobial Activities
2723
Potassium Salts of N,N-Disubstitued Dithiocarbamic Acids (6)
Potassium hydroxide (0.02 mol) was dissolved in ethanol (80 mL) with
constant stirring. After the addition of the secondary amine (0.02 mol),
the mixture was cooled in an ice bath and carbon disulphide (0.02 mol)
was added dropwise with stirring. The reaction mixture was agitated
for 1 h at r.t. and the solvent was evaporated under reduced pressure.
The product was obtained from washing of the precipitate with ether.17
1-[(N,N-Disubstituted Thiocarbamoylthio)acetyl]-3,5-diaryl-2-
pyrazolines (7)
A mixture of 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines (5) (0.01 mol) and
the appropriate potassium salts of secondary amine dithiocarbamic
acids (6) (0.01 mol) was stirred in acetone at room temperature for 4 h.
The solvent was evaporated and the residue was washed with water
and recrystallized from ethanol.14
Some characteristics and spectral data of the synthesized compounds
are shown in Table I and Table II, respectively.
Microbiology
Microdilution broth susceptibility assay was used for the antimicrobial
evaluation of the compounds.18 Stock solutions of the samples were
prepared in dimethylsulfoxide. Dilution series using sterile distilled
water were prepared in micro test tubes that were transferred to 96-
well microtiter plates. Overnight grown bacterial and C. albicans sus-
pensions in double-strength Mueller-Hinton broth were standardized
to 108 CFU/mL using McFarland No. 0.5 standard solution. 100 µl of
each microorganism suspension then was added into the wells. The
last well chain without a microorganism was used as a negative con-
trol. Sterile distilled water and the medium served as a positive growth
control. After incubation at 37◦C for 18–24 h, the first well without tur-
bidity was determined as the Minimal Inhibitory Concentration (MIC).
Chloramphenicol was used as standard antibacterial agent whereas
ketoconazole was used as antifungal agent.
The following were used as a test microorganisms: Staphylococcus
aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa
(ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida albicans
(NRRL-27077).
The observed data on the antimicrobial activity of the compounds
and control drugs are given in Table III.

2724
G. Turan-Zitouni et al.
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