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Synthesis and Antibacterial Activity of tert-Butyl [1-benzyl-2[4-aryl-2-thiazolylhydrazono]ethyl]carbamate Derivatives.

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310
Arch. Pharm. Chem. Life Sci. 2007, 340, 310 – 314
Full Paper
Synthesis and Antibacterial Activity of tert-Butyl [1-benzyl-2[(4aryl-2-thiazolyl)hydrazono]ethyl]carbamate Derivatives
Glhan Turan-Zitouni1, Jean-Alain Fehrentz2, Pierre Chevallet2, Jean Martinez2, Zafer Asim
Kaplancıklı1, Ahmet zdemir2, Muhittin Arslanyolu3, and Mehmet Taha Yıldız3
1
Anadolu University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Eskisehir, Turkey
Montpellier University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry LAAP, CNRS-UMR,
Montpellier, France
3
Anadolu University, Faculty of Science, Department of Biology, Eskisehir, Turkey
2
The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent
additional urgency to microbiological research and new antibacterial compound development.
For this purpose, new tert-butyl[1-benzyl-2[(4-aryl-2-thiazolyl)hydrazono]ethyl]carbamate derivatives were synthesized and evaluated for antibacterial activity. The reaction of Boc-L-phenylalaninal with thiosemicarbazide gave the thiosemicarbazone which furnished the title compounds
by reaction with phenacyl bromides. The newly synthesized compounds were screened for antibacterial activity and toxicity. While microdilution broth susceptibility assay was used for the
antibacterial activity evaluation of the compounds against the strains E. coli (NRRL B-3704), M.
luteus (NRRL B-4375), B. cereus (NRRL B-3711), P. aeruginosa (NRRL B-23), and S. fecalis (NRRL B14617), the Artemia salina 96-well assay was used to determine cytotoxicities of the compounds.
Observations obtained from the bioassays showed that some of the compounds are highly active
against E. coli, M. luteus, and B. cereus when compared with the control agent and showed low
toxicity.
Keywords: Amino acid / Antibacterial activity / Thiazole /
Received: November 29, 2006; accepted: April 12, 2007
DOI 10.1002/ardp.200600200
Introduction
The emergence of multi-drug resistant strains of bacterial pathogens is a significant clinical problem. Efforts to
improve or expand the utility of existing antibiotics have
been only moderately successful; hence, there is an
urgent need for novel classes of antibacterial agents that
act on previously unexploited biochemical targets essential to the pathogen life-cycle. In order to overcome these
problems, new agents should preferably have chemical
characteristics that clearly differ from those of existing
agents. In drug-designing programs an essential compo-
Correspondence: Glhan Turan-Zitouni, Department of Pharmaceutical
Chemistry, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir,
Turkey.
E-mail: gturan@anadolu.edu.tr
Fax: +90 222 335-0750
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2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
nent of the search for new leads is the synthesis of molecules, which are novel yet resemble known biologically
active molecules by virtue of the presence of critical
structural features [1 – 4].
Antibacterial peptides (AMPs) have recently received
increasing attention for being the potential substitute
for antibiotics. They display a large heterogeneity in primary and secondary structures but share common functions such as the cytotoxicity and selectivity. Although
their precise mechanism of action is not fully understood, AMPs are believed to kill the target cell by destabilizing the ordered structure of the cell membrane via
either a “barrel stave” mechanism or a “carpet-like”
mechanism. The mechanism of action differs from conventional antibiotics and their broad spectrum of antibacterial activities makes AMPs potentially useful for
pharmacological application and commercial exploitation [5 – 6].
Arch. Pharm. Chem. Life Sci. 2007, 340, 310 – 314
One of the important members of this group is Escherichia coli peptide antibiotic microcin B17 (MccB17).
Among the novel class of anti-infectives not currently
used clinically are the thiazole peptides. They comprise a
family of non ribosomally synthesized compounds classified by the architecture of their thiazole heterocycles [7 –
10].
MccB17 causes double-stranded DNA breaks in a DNA
gyrase-dependent fashion, analogous to the inhibition of
bacterial type-II DNA topoisomerases by antibiotics such
as the quinolones. This peptide antibiotic takes its eventual form after post-translational modification which
includes heterocyclization of some amino acid moieties.
After the modification some of these moieties converted
to a thiazole ring bearing amino acid residues [11 – 16]. It
has been shown that these moieties have been identified
as probable partners for interaction with DNA and thiazole moieties in MccB17 are presumed to play a critical
role in this interaction, because the rest of the molecule
essentially constitutes a polyglycine residue [17].
In view of these data, we aimed the synthesis of a novel
amino acid residue bearing a thiazole ring which could
mimic the above mentioned compounds and possesses
antibacterial activity. Hence, amino acid-thiazole combination, i. e. alanine, valine, and proline-thiazole, previously produced successful antibacterials [18], led us to
focus on L-phenylalanine-thiazole derivatives, which are
readily synthesized and evaluated for antibacterial activities.
Results and discussion
In the present work, nine new compounds were synthesized. tert-Butyl[1-benzyl-2-thiosemicarbazonoethyl]carbamate 1 was prepared by reacting Boc-L-phenylalaninal
with thiosemicarbazide in accordance with the method
described in the literature [19 – 20]. The reaction of tertbutyl[1-benzyl-2-thiosemicarbazonoethyl]carbamate
1
and phenacyl bromides gave the tert-butyl[1-benzyl-2-[(4aryl-2-thiazolyl)hydrazono]ethyl] carbamate derivatives
2a – i are shown in Scheme 1 and some characteristics of
the compounds in Table 1.
The formula of compounds 2a – i have been confirmed
by elemental analyses and their structures determined
by IR, 1H-NMR, and FAB+-MS spectral data. The IR data
were analytically helpful and provided good evidence for
the formation of the expected structures. N-H, C=O, C=N,
C=C, and C-O-C functions absorbed strongly in the
expected regions: N-H at 3428-3499 cm – 1, C=O at 1697 –
1685 cm-1, C=N and C=C at 1563 – 1505 cm – 1, and C-O-C at
1169 – 1157 cm – 1, respectively. The 1H-NMR spectra
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2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Antibacterial Activity of Carbamate Derivatives
311
Table 1. Some characterizations of the compounds.
Comp.
R1
R2
R3
Yield
(%)
M.p.
(8C)
MW
2a
2b
2c
2d
2e
2f
2g
2h
2i
H
H
H
H
H
H
OH
OH
H
H
Cl
CH3
OCH3
OH
NO2
H
H
Cl
H
H
H
H
H
H
Cl
OCH3
Cl
69
78
73
71
63
84
61
62
79
116 – 118
154 – 156
148 – 150
106 – 108
124 – 126
160 – 162
230 – 232
168 – 170
144 – 146
422
456.5
436
452
438
467
472.5
468
491
Scheme 1. The general synthesis route of presented compounds.
showed t-butyl protons at 0.90 – 1.50 ppm, as singlet or
multiplet, in all nine compounds synthesized. The CH2
protons of benzyl were observed at 2.70 – 3.10 ppm as
multiplet and NH-CH at 4.15 – 4.45 ppm as singlet or
broad. CO-NH and CH=N protons appeared at aromatic
region with aromatic protons. All the other aromatic and
aliphatic protons were observed at expected regions. All
compounds gave satisfactory elemental analysis. Mass
spectra (MS (FAB)) of compounds showed M+1 peaks, in
agreement with their molecular formula.
MICs were recorded as the minimum concentration of
a compound that inhibits the growth of tested microorganisms. As shown in Table 2, all of the compounds were
mostly effective against E. coli with MIC values almost
two orders of magnitude lower than the positive control
chloramphenicole. Against M. luteus, compounds 2g and
2h showed potency approximately 30-fold better than
chloramphenicole, 2d and 2f four-times better, whereas
2b and 2i were at the same level of activity as chloramphenicole. Furthermore, compounds 2g and 2h also
exhibited a very strong antibacterial activity against B.
cereus but they possessed a comparable activity against
both S. feacalis and P. aeruginosa to the positive control
agent.
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G. Turan-Zitouni et al.
Arch. Pharm. Chem. Life Sci. 2007, 340, 310 – 314
Table 2. MIC values (lg/mL) of the compounds.
General procedure for synthesis of the compounds
Compound
tert-Butyl-(1-benzyl-2-thiosemicarbazonoethyl)carbamate 1
E. coli
2a
0.48A
2b
0.48A
2c
0.48A
2d
0.97
2e
0.48A
2f
0.48A
2g
0.48A
2h
0.48A
2i
0.48A
Chloramphenicol 62.50
M. luteus
B. cereus
P. aeroginosa S. fecalis
62.50
15.62
62.50
3.90
62.50
3.90
0.48A
0.48A
15.62
15.62
62.50
62.50
125
125
125
62.50
0.48A
0.48A
125
31.25
125
125
62.50
125
125
125
62.50
62.50
125
31.25
125
125
125
125
125
125
62.50
31.25
125
31.25
Table 3. Toxicity assay.
Compound
LD50
(lg/mL)
Upper 95% lim. Lower 95% lim.
(lg/mL)
(lg/mL)
2a
2b
2c
2d
2e
2f
2g
2h
2i
1000
707
A1000
378.90
217.64
1000
1000
50.76
116.63
–
794
–
524.51
288.17
–
–
68.30
144.57
–
629
–
273.76
164.37
–
–
37.71
94.09
A mixture of Boc-L-phenylalaninal and thiosemicarbazide, in
ethanol (50 mL) were refluxed for 1 h. The solid, upon cooling,
was filtered and crystallized from ethanol
tert-Butyl-[1-benzyl-2-[(4-aryl-2thiazolyl)hydrazono]ethyl]carbamate 2
Equimolar amount of tert-butyl(1-benzyl-2-thiosemicarbazonoethyl)carbamate 1 (0.01 mol) and phenacyl bromides (0.01 mol)
were stirred in ethanol at room temperature for 8 h. The solid
was filtered and crystallized from ethanol. Some characteristics
of the synthesized compounds are shown in Table 1.
tert-Butyl-[1-benzyl-2-[4-(4-phenyl-2thiazolyl)hydrazono]ethyl]carbamate 2a
IR [m, cm – 1, KBr]: 3486-3440 (N-H), 1693 (C=O), 1559-1515 (C=N,
C=C), 1169 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 0.90 –
1.50 (9H, m, tert-butyl protons), 2.70 – 3.05 (2H, m, CH2 protons of
benzyl), 4.20 – 4.45 (1H, m, NH-CH), 7.00 – 8.00 (13H, m, CO-NH,
CH=N and aromatic protons), 11.75 (1H, s, N-NH). MS (FAB) [M+1]:
m/z 423. For C23H26N4O2S calculated: 65.38% C, 6.20% H, 13.26%
N; found: 65.31% C, 6.16% H, 13.22% N.
tert-Butyl-[1-benzyl-2-[[4-(4-chlorophenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2b
Based on the limited number of compounds evaluated,
it appears that ortho-hydroxyl substitution on the phenyl
ring attached to the thiazole moiety has made a good
contribution to the antibacterial activity in this series of
L-phenylalane-thiazole combination.
The cytotoxicity results are shown in Table 3. As can be
seen, the antibacterial activity does not correlate with
the toxic effect, implying that these compounds may
have selectively interacted with bacteria instead of host
cells. It is worth noting that compound 2g is one of the
least toxic molecules.
Experimental
Chemistry
All reagents were used as purchased from commercial suppliers
without further purification. Melting points were determined
by using an Electrothermal 9100 digital melting point apparatus and were uncorrected (Electrothermal, Essex, UK). The compounds were checked for purity by TLC on silica gel 60 F254. Spectroscopic data were recorded on the following instruments: IR,
Shimadzu 435 IR spectrophotometer (Shimadzu, Tokyo, Japan);
1
H-NMR, Bruker 250 MHz NMR spectrometer (Bruker Bioscience,
Billerica, MA, USA) in DMSO-d6 using TMS as internal standard;
Elemental analyses were performed on a Perkin Elmer EAL 240
elemental analyser (Perkin-Elmer, Norwalk, CT, USA); MS-FAB,
VG Quattro mass spectrometer (Fisons Instruments Vertriebs
GmbH, Mainz, Germany).
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2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
IR [m, cm – 1, KBr]: 3499 – 3435 (N-H), 1695 (C=O), 1555 – 1510 (C=N,
C=C), 1165 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.30 (9H,
s, tert-butyl protons), 2.75 – 3.00 (2H, m, CH2 protons of benzyl),
4.35 (1H, s, NH-CH), 7.00 – 7.10 (8H, m, C5-H of thiazole, CO-NH,
CH=N and aromatic protons of benzyl), 7.80 – 7.90 (4H, m, phenyl
protons), 11.75 (1H, s, N-NH). MS (FAB) [M+1]: m/z 457. For
C23H25ClN4O2S calculated: 60.45% C, 5.51% H, 12.26% N; found:
60.49% C, 5.55% H, 12.29% N.
tert-Butyl-[1-benzyl-2-[[4-(4-methylphenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2c
IR [m, cm – 1, KBr]: 3455 – 3428 (N-H), 1692 (C=O), 1553 – 1516 (C=N,
C=C), 1167 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.35 (9H,
s, tert-butyl protons), 2.35 (3H, s, CH3), 2.75 – 3.10 (2H, m, CH2 protons of benzyl), 4.30 – 4.45 (1H, br, NH-CH), 7.15-7.40 (8H, m, C5-H
of thiazole, CO-NH, CH=N and aromatic protons of benzyl), 7.807.90 (4H, d, phenyl protons), 11.75 (1H, s, N-NH). MS (FAB) [M+1]:
m/z 437. For C24H28N4O2S calculated: 66.03% C, 6.46% H, 12.83%
N; found: 66.00% C, 6.42% H, 12.79% N.
tert-Butyl-[1-benzyl-2-[[4-(4-methoxyphenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2d
IR [m, cm – 1, KBr]: 3480 – 3432 (N-H), 1690 (C=O), 1551 – 1506 (C=N,
C=C), 1159 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.30 (9H,
s, tert-butyl protons), 2.75 – 3.00 (2H, m, CH2 protons of benzyl),
3.75 (3H, s, OCH3), 4.30 – 4.40 (1H, br, NH-CH), 6.90 (2H, d, J = 8.87
Hz, phenyl protons), 7.10 (1H, s, C5-H of thiazole), 7.15 – 7.40 (7H,
m, CO-NH, CH=N and aromatic protons of benzyl), 7.70 (2H, d, J =
8.73 Hz, phenyl protons), 11.70 (1H, s, N-NH). MS (FAB) [M+1]: m/z
453. For C24H28N4O3S calculated: 63.69% C, 6.24% H, 12.38% N;
found: 63.61% C, 6.29% H, 12.33% N.
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Arch. Pharm. Chem. Life Sci. 2007, 340, 310 – 314
tert-Butyl-[1-benzyl-2-[[4-(4-hydroxyphenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2e
IR [m, cm – 1, KBr]: 3495 – 3427 (N-H), 1696 (C=O), 1554 – 1505 (C=N,
C=C), 1161 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.30 (9H,
s, tert-butyl protons), 2.70 – 3.10 (2H, m, CH2 protons of benzyl),
4.20 – 4.40 (1H, br, NH-CH), 6.75 (2H, d, J = 8.64 Hz, phenyl protons), 7.00 (1H, s, C5-H of thiazole), 7.10 – 7.40 (7H, m, CO-NH,
CH=N and aromatic protons of benzyl), 7.60 (2H, d, J = 8.64 Hz,
phenyl protons), 11.75 (1H, s, N-NH). MS (FAB) [M+1]: m/z 439. For
C23H26N4O3S calculated: 62.99% C, 5.98% H, 12.78% N; found:
62.96% C, 5.96% H, 12.79% N.
tert-Butyl-[1-benzyl-2-[[4-(4-nitrophenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2f
IR [m, cm – 1, KBr]: 3489 – 3441 (N-H), 1691 (C=O), 1557 – 1518 (C=N,
C=C), 1168 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.10 –
1.50 (9H, m, tert-butyl protons), 2.70 – 3.05 (2H, m, CH2 protons of
benzyl), 4.15 – 4.40 (1H, m, NH-CH), 7.10 – 7.40 (7H, m, CO-NH,
CH=N and aromatic protons of benzyl), 7.70 (1H, s, C5-H of thiazole), 8.10 (2H, d, J = 8.81 Hz), phenyl protons), 8.30 (2H, d, J =
8.87 Hz, phenyl protons), 11.85 (1H, s, N-NH). MS (FAB) [M+1]: m/z
468. For C23H25N5O4S calculated: 59.09% C, 5.39% H, 14.98% N;
found: 59.01% C, 5.41% H, 14.95% N.
tert-Butyl-[1-benzyl-2-[[4-[(2-hydroxy-5-chloro)phenyl)]-2thiazolyl]hydrazono]ethyl] carbamate 2g
IR [m, cm – 1, KBr]: 3490 – 3439 (N-H), 1689 (C=O), 1548 – 1521 (C=N,
C=C), 1160 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.30 (9H,
s, tert-butyl protons), 2.75 – 3.10 (2H, m, CH2 protons of benzyl),
4.30 – 4.45 (1H, br, NH-CH), 6.90 – 7.90 (11H, m, CO-NH, CH=N and
aromatic protons), 11.20 (1H, s, OH), 11.90 (1H, s, N-NH). MS (FAB)
[M+1]: m/z 473. For C23H25ClN4O3S calculated: 58.41% C, 5.33% H,
11.85% N; found: 58.44% C, 5.31% H, 11.82% N.
Antibacterial Activity of Carbamate Derivatives
313
were prepared in dimethylsulfoxide (DMSO). Tested compounds
and standard agent chloramphenicol, were prepared within the
concentration range of 0.48 – 1000 lg/mL, by dissolving in
DMSO. Dilution series using sterile distilled water were prepared
in micro-test tubes that were transferred to 96-well microtiter
plates. Overnight grown bacterial suspensions in doublestrength Mueller – Hinton broth were standardized to 108 CFU/
mL using McFarland No: 0.5 standard solution. An amount of
100 lL of each microorganism suspension was then added into
the wells. The last well-chain without microorganism was used
as a negative control. Sterile distilled water and the medium
served as a positive growth control. After incubation at 378C for
18 – 24 h the first well without turbidity was determined as the
minimal inhibitory concentration (MIC). Tested microorganism
strains were; Escherichia coli (NRRL B-3704), Micrococcus luteus
(NRRL B-4375), Bacillus cereus (NRRL B-3711), Pseudomonas aeruginosa (NRRL B-23), Streptococcus feacalis (NRRL B-14617). The
observed data on the antibacterial activity of the compounds
and control drugs are given in Table 2.
Toxicity
It is known that the shrimp lethality assay is considered a useful
tool for preliminary assessment of toxicity and gives reliable
results in correlation with rodent and human acute oral toxicity
data [23, 24], Artemia salina 96-well assay has been used to determine the cytotoxicity levels of the compounds [25]. Tested compounds were prepared within the range of 1.95 – 1000 lg/mL by
dissolving in DMSO. Tests were carried out as described in the
related reference [25]. The LD50 values and 95% confidence intervals of the compounds were calculated with the TSK program
[26 – 27]. The results are given Table 3.
References
tert-Butyl-[1-benzyl-2-[[4-[(2-hydroxy-5-methoxy)phenyl)]-2-thiazolyl]hydrazono]ethyl] carbamate 2h
IR [m, cm – 1, KBr]: 3472 – 3447 (N-H), 1697 (C=O), 1563 – 1513 (C=N,
C=C), 1164 (C-O-C). 1H-NMR (250 MHz, DMSO-d6, d ppm): 1.30 (9H,
s, tert-butyl protons), 2.75 – 3.05 (2H, m, CH2 protons of benzyl),
3.90 (3H, s, OCH3), 4.25 – 4.40 (1H, br, NH-CH), 6.85 – 7.60 (11H, m,
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tert-Butyl-[1-benzyl-2-[[4-(3,4-dichlorophenyl)-2thiazolyl]hydrazono]ethyl]carbamate 2i
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antibacterial, synthesis, butyl, benzyl, thiazolylhydrazono, activity, tert, ethyl, aryl, carbamate, derivatives
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