Inorganic Chemistry Communications 14 (2011) 1550–1553

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Inorganic Chemistry Communications

j o u r n a l h o m e p a g e : w w w. e l s ev i e r. c o m / l o c a t e / i n o c h e

Mini-Review

Synthesis, characterization and antimicrobial activity of salicylaldehyde

benzenesulfonylhydrazone (Hsalbsmh)and its Nickel(II), Palladium(II),
Platinum(II), Copper(II), Cobalt(II) complexes
Halime Güzin Aslan a,⁎, Servet Özcan b, Nurcan Karacan c
a
Department of Chemistry, Faculty of Sciences, Erciyes University 33053 Melikgazi-Kayseri, Turkey
b
Department of Biology, Faculty of Sciences, Erciyes University 33053 Melikgazi-Kayseri, Turkey
c
Department of Chemistry, Faculty of Arts Sciences, Gazi University 06500 Teknikokullar, Ankara, Turkey

a r t i c l e i n f o a b s t r a c t

Article history: In this study Benzenesulfonicacid-1-methylhydrazide (bsmh) derivatives such as salicylaldehyde benzene-
Received 22 March 2011 sulfonylhydrazone (Hsalbsmh) and its Ni(II), Pd(II), Pt(II), Cu(II), Co(II) complexes were synthesized for the
Accepted 25 May 2011 first time. The structure of these complexes was investigated by using elemental analyses, the FT-IR, LC–MS
Available online 2 June 2011
and UV–VIS spectrophotometric methods, magnetic susceptibility and conductivity measurement techniques.
The complexes were found to have general compositions [ML2]. Using disk diffusion methods all the
Keywords:
Antimicrobial activity
synthesized complexes were evaluated in vitro as antimicrobial agents against representative strains of gram-
Sulfonamides positive (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 11778, Enterococcus faecalis ATCC 29212,
Aromatic sulfonamide Bacillus subtilis ATCC 6633, Staphylococcus epidermidis ATCC 12228, Enterobacter aerogenes ATCC 13048) and
Sulfonamide complexes gram-negative bacteria (Pseudomonas fluorescens ATCC 49838, Klebsiella pneumoniae ATCC 13883, Escherichia
coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853) and as an antifungal agent against Candida albicans
(ATCC 90028). All the bacteria and fungus studied were screened against some antibiotics to compare with our
chemical zone diameters.
Published by Elsevier B.V.

Contents

Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Experimental . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Physical measurements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
General procedure for the synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Synthesis of salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Synthesis of Ni(II), Pd(II), Pt(II), Cu(II), Co(II) complexes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Biological activity: in vitro evaluation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Determination of inhibition zones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1551
Results and discussion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
The characterization of the compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
FT-IR spectra . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
NMR spectra. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
Mass spectra. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
Electronic spectra and magnetic behavior . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1552
Biological activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1553
Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1553
Acknowledgments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1553
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1553

⁎ Corresponding author. Tel.: + 90 5326887509; fax: + 90 3524374933.

E-mail address: guzina@erciyes.edu.tr (H.G. Aslan).

1387-7003/$ – see front matter. Published by Elsevier B.V.

doi:10.1016/j.inoche.2011.05.024
 H.G. Aslan et al. / Inorganic Chemistry Communications 14 (2011) 1550–1553
Introduction
The sulfonamide \SO2NH\group occurs in numerous biologically
active compounds which include antimicrobial drugs, saluretics,
carbonic anhydrase inhibitors, insulin-releasing sulfonamides, anti-
thyroid agents, antitumor drugs and in a number of other biological
activities. Furthermore, low cost and low toxicity are their principle
advantages [1–15].
Methanesulfonamide derivatives possess DNA-binding ability,
show cytostatic effects, and some of them, like Amsacrine, are used
in cancer chemotherapy treatment [16–19]. Some sulfonylhydrazines
are known to have antineoplastic effects which prevent malign cells
from growing and spreading [20]. Imidosulfonylhydrazones have
antibacterial and antinociceptive properties [21]. Acidic sulfonyl
hydrazone derivatives have analgesic and anti-inflammatory proper-
ties [22]. Benzaldehyde arylsulfonylhydrazones possess antineoplas-
tic activity against human stomach cancer SGC 7901 cells [23]. 4-
substituted benzenesulfonylhydrazone has been found to have
antibacterial activity [24].
A further extension of this area was made by the formation of the
silver (I) complex of sulfonylamide which emphasized the role of metals
in enhancing biological activity [25]. The transition metal complexes of
hydrazides and sulfonamides also have applications in chemotherapy.
The synergetic action of sulfonamides with trimethoprim has brought
about an enormous resurgence of sulfonamide usage in many areas over
the past decade.
This prompted us to synthesize a series of novel symmetric
aromatic sulfonamide complexes. We obtained a series of new
sulfonamide complexes (1–5) and characterized their structure by
FT-IR, LC/MS, UV–VIS, magnetic susceptibility and elemental analysis
techniques. We also studied their antibacterial activities against
gram-positive and gram-negative bacteria and as an antifungal agent
using the disk diffusion method. All of the bacteria and fungus studied
were screened against standard antibiotics to compare them with our
chemical zone diameters.
The structural formula of the series of aromatic sulfonamide
complexes (1–5) is given in Fig. 1.
Experimental
Physical measurements
The infrared spectra of the compounds as KBr-disks were recorded
in the range of 4000–400 cm − 1 with a Mattson 1000 FT-IR
spectrometer. LC/MS-APC1 was recorded on an AGILENT 1100. UV–
VIS spectra were recorded on a UNİCAM-UV 2–100 spectrophotom-
eter. The melting point was recorded on an Opti MELT 3 hot stage
apparatus. TLC was conducted on 0.25 mm silica gel plates (60 F254,
Fig. 1. Fig. 1. M_Co(II), Ni(II), Cu(II), Pd(II), Pt(II) trans-bis(salicylaldehydebenzen-
sülfonyl-1-methylhydrazonato) metal(II).
1551
Merck). Visualization was made with ultraviolet light. The molar
magnetic susceptibilities were measured on powdered samples using
the Gouy method. The molar conductance measurements were
carried out using a Siemens WPA C 35 conductometer. All extracted
solvents (all from Merck) were dried over anhydrous Na2SO4 and
evaporated with a BUCHI rotary evaporator. Reagents were obtained
commercially from Aldrich (ACS grade) and used as received.
General procedure for the synthesis
Synthesis of salicylaldehyde benzenesulfonylhydrazone (Hsalbsmh)
A solution of bsmh [26] (4.95 ml, 50 mmol) in 5 ml ethanol was
mixed with a solution of salicylaldehyde (5.31 ml, 50 mmol) in 5 ml
ethanol and stirred all night. The product was recrystallized from
acetonitrile three times. This resulted in a light yellow solid which is
stable at normal conditions and soluble only in DMSO and DMF [26].
Synthesis of Ni(II), Pd(II), Pt(II), Cu(II), Co(II) complexes
All complexes were prepared by the following general method. A
sample of anhydrous MCl2 (M: Ni, Pd, Pt, Cu, Co) (0.01 mol) was
dissolved in a mixture of ethanol and DMSO and a solution of
hydrazone derivatives (0.02 mol, 7.8 g) in a mixture of DMSO and
NaOH solution in ethanol (0.02 mol, 0.8 g) was added. The reaction
mixture was heated at 40 °C for 30 min and left in an ice bath for 3 h.
The solid complexes which formed were collected by filtration,
washed with a small volume of ethanol and ether, and then dried in a
desiccator over CaCl2[26]. The analytical and physical data for the
Hsalbsmh ligand and its complexes are given in Table 1.
Biological activity: in vitro evaluation
The biological activity of the synthesized sulfonamide derivatives
was individually screened against a panel of microorganisms, including
gram-positive (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC
11778, Enterococcus faecalis ATCC 29212, Bacillus subtilis ATCC 6633,
Staphylococcus epidermidis ATCC 12228, Enterobacter aerogenes ATCC
13048) and gram-negative bacteria (Pseudomonas fluorescens ATCC
49838, Klebsiella pneumoniae ATCC 13883, Escherichia coli ATCC 25922,
Pseudomonas aeruginosa ATCC 27853) and yeast (Candida albicans ATCC
90028). Cultures were obtained from Erciyes University, Faculty of
Sciences, Department of Biology. Bacterial strains were cultured
overnight at 35 °C in Triptic Soy Broth (TSB) and the yeast was cultured
overnight at 35 °C in Yeast Peptone Dextrose Broth (YPDB) in a rotary
shaker at 200 rpm. Overnight cultures were then transferred to a fresh
medium and the turbidity of all broth cultures was adjusted to 0.1
absorbance at 640 nm on a spectrophotometer. These stock cultures
were stored in the dark at 4 °C during the study.
Determination of inhibition zones
The disk diffusion antibacterial screenings [27–31] of synthesized
sulfonamide derivatives dissolved in DMSO were performed using
Miller-Hinton Agar (MHA) for the bacterial strains and Yeast Peptone
Dextrose Agar (YPDA) for the yeast cells. 100 μl of the culture
suspensions adjusted to OD640 0.1 (equivalent to 0.5 Mc Farland
Turbidity) was swabbed over the entire surface of the medium
(Bauer-Kirby, 1966; NCCLS 2000). Sterile 6-mm-diameter disks
(1.2 mm thickness Whatman filter paper) were impregnated with
50 μl dissolved extracts (including 1.2 mg total extract per disk) and
placed onto MHA or YPDA. Negative controls were prepared by using
50 μl of DMSO alone. For the bacterial cells ampicilin (50 μg/disk),
trimethoprim (30 μg/disk), tetracycline (30 μg/disk) on MHA, and for
the yeast cells miconazole (40 μg/disk) and nystatin (30 μg/disk) on
YPDB were used as reference standards to determine the sensitivity of
each strain. The inoculated plates were incubated at 35 °C for 18–24 h.
Antibacterial activity was measured as the diameter (mm) of the clear
1552 H.G. Aslan et al. / Inorganic Chemistry Communications 14 (2011) 1550–1553

Table 1
Analytical and physical data for Hsalbsmh ligand and complexes.

Comp. %C Found (Calculated) %H %N %S %Met E.N (°C) Empirical formula (formula weight) Color B.M Conductivity (μs)

Hsalbsmh 57.916 4.860 9.648 11.042 – 167 C14H14N2SO3 L.Yellow – –

(57.931) (4.880) (9.663) (11.022) 290.336
Ni(sal)2 52.740 4.134 8.768 10.085 9.180 258 C28H26N4S2O6Ni L.Brown 0.34 1.14
(52.765) (4.111) (8.790) (10.061) (9.208) 637.361
Pd(sal)2 49.072 3.844 8.159 9.380 15.536 395 C28H26N4S2O6Pd Brown 0 0.90
(49.090) (3.825) (8.178) (9.360) (15.563) 684.032
Pt(sal)2 43.446 3.405 7.259 8.298 25.230 299 C28H26N4S2O6Pt Orange 0 0.50
(43.464) (3.387) (7.240) (8.288) (25.212) 773.748
Cu(sal)2 52.350 4.094 8.741 9.998 9.904 389 C28H26N4S2O6Cu D.Yellow 2.6 0.58
(52.367) (4.080) (8.724) (9.985) (9.894) 642.213
Co(sal)2 52.760 4.096 8.801 10.050 9.228 310 C28H26N4S2O6Co Brown 3.89 0.62
(52.745) (4.110) (8.787) (10.057) (9.242) 637.601

zone of growth inhibition. Four disks per plate were used and each IR spectrophotometer observation of the ν(C\O) stretching vibration at
test was run in duplicate. 1258 cm − 1 and the ν(C_N) stretching vibration at 1659 cm − 1
convinced us to propose that the structure of phenol-imine was in the
Results and discussion solid phase. The peaks of H and C atoms belonging to CH3, which is
connected to the N atom, were observed at 2.60 ppm and 35.22 ppm,
The results of elementary analysis showed 1:2 (metal/ligand) respectively. The aromatic C atom peaks were as follows: 158.22–117.13.
stoichiometry for all the complexes. The analytical results were in
good agreement with those required by the general formula [ML2].
The molar conductivity (Λm) of the 10 − 3 M solutions of the Mass spectra
complexes in DMSO at 25 °C was measured and all complexes were LC/MS shows that Ni(salbsmh)2, Pd(salbsmh)2, Cu(salbsmh)2, and
found to be of non-electrolytic nature. Co(salbsmh)2 give the molecular ion [ML2] + at the desired positions:
The Hsalbsmh ligand and its complexes which we studied have not 637.20, 685.40, 642.30, and 637.95 m/z and Pt(salbsmh)2 gives the
been previously reported in the literature. molecular ion, [PdL2+ NH4] + at 790.70 m/z. Ni (salbsmh)2 gives the
isotope abundance at the desired positions [M ++ 2] [Ni metal isotope
The characterization of the compounds abundance] at 639.2 m/z and Hsalbsmh gives the molecular ion
[Hsalbsmh + Na] + at 313.10 m/z Separately, all complexes and
FT-IR spectra Hsalbsmh give the fragmentation of the C6H5 group, which is
The wave number of the selected vibration of the IR spectra of the observed at 79.2 m/z.
compounds is listed in Table 2. The IR spectra of the compounds were
found to be very similar to each other. The most characteristic
vibrations of the compounds are as follows: the asymmetric (vas) and Electronic spectra and magnetic behavior
symmetric (vs) stretching vibrations of the SO2 groups were observed The significant electronic spectra of the ligand and complexes are
at ~1231 and ~ 1250 cm − 1, ~ 1170 and ~1186 cm − 1 respectively. The recorded in DMSO. The important bands of the ligand are observed in
C_N group stretching vibration band was found between 1601 and the region of 430–332 nm.
1659 cm − 1. The magnetic moments of the complexes (as B.M.) were measured
The (C_N) stretching vibration band of Hsalbsmh is observed at at room temperature. Nickel, palladium and platinum complexes have
1650 cm− 1. Upon the complex formation, the (C_N) stretching diamagnetic characters, and therefore their complexes have a square
vibration band is shifted to a lower wave number (between 1647 and planar geometry. The effective magnetic moment values for Cu
1601 cm− 1). (salbsmh)2 and Co(salbsmh)2 complexes were 2.06 and 3.89 B.M.,
The (C\O) stretching vibration band of Hsalbsmh is observed respectively. Low magnetic moment values support tetrahedral
1258 cm− 1. Upon the complex formation, the (C\O) stretching configurations for the Cu and Co complexes [32].
vibration band is shifted to a higher wave number (between 1366 The magnetic moments of complexes (as B.M.) were measured at
and 1400 cm− 1). room temperature. The magnetic moment value (0.34 B.M.) for Ni
(salbsmh)2, as well as the broad band in its electronic spectrum
NMR spectra centered at 363 nm, suggested a square planar geometry around the
The 1H-NMR spectrum of the Hsalbsmh compound showed that the nickel(II) ion. The observed band was due to the 1B1g → 1A1g and
1
OH proton had a wide peak at 10.30 ppm, and the N_CH proton at A2g → 1A1g transitions in the square planar geometry. The electronic
8.60 ppm. Based on these data, the structure of the phenol-imine spectrum of the Pd(II) and Pt(II) complexes 353–354 nm, attributed
compound of Hsalbsmh was in the DMSO solution. On the other hand, the to the 1A2g → 1B1g and 3B1g → 1A1g transitions respectively, indicated a
square planar environment around the metal ions. The observed
magnetic moments of the Palladium (II) and Platinum (II) complexes
Table 2 were 0 B.M. The electronic spectrum of the Cu (II) complex consisted
Wave number (cm− 1) of selected vibration of the compounds. of band 354 nm, arising from the 2Eg → 1T2g transition similar to that
Compound vC\O vas(SO2) vs(SO2) vC_N found for the tetrahedral complexes. At room temperature, the
magnetic moment (2.06 B.M.) corresponded to a tetrahedral
Hsalbsmh 1258 1250 1180 1659
Ni(salbsmh)2 1366 1244 1186 1633 symmetry. The magnetic moment value (3.89 B.M.) for Co(salbsmh)2,
Pd(salbsmh)2 1367 1231 1173 1621 the broad band in its electronic spectrum centered at 425 nm,
Pt(salbsmh)2 1368 1230 1170 1621 suggested a tetrahedral geometry around the Co(II) ion. The observed
Cu(salbsmh)2 1400 1240 1175 1647 band was due to the 4 T1(F) → 4A2 transition in the tetrahedral
Co(salbsmh)2 1375 1243 1176 1601
geometry [32].
 H.G. Aslan et al. / Inorganic Chemistry Communications 14 (2011) 1550–1553 1553

Table 3
Inhibition zone of complexes by disk diffusion method (mm).

Ni Pd Pt Cu Co Hsalbsmh Tetrasilin (30 μg) Trimetoprim (30 μg) Miconazole (30 μg) Nystatin (40 μg)

P. fluorescens 15 11 11 0 0 12 19 0 0 0
P.aeruginosa 0 10 9 0 0 6 12 0 0 0
E. coli 10 10 11 0 0 13 23 0 0 0
K. pneumonia 9 12 10 0 0 6 23 31 0 0
E.aerogenes 0 13 14 0 0 6 19 29 0 0
S. aureus 0 15 12 0 9 13 0 27 0 0
B. cereus 0 14 13 0 9 11 19 0 0 0
B. subtilis 0 18 17 0 0 9 26 20 0 0
S. epidermidis 0 14 13 0 12 14 0 37 0 0
E. faecalis 0 14 13 0 0 11 0 28 0 0
C. albicans 0 12 10 0 0 14 0 0 26 18

Inhibition zone (mm, 140 μg/disk) M(salbsmh)2.

Biological activity
In the present study, the antimicrobial activities of compounds
were screened against various pathogens in vitro by disk diffusion
methods. Tetracycline, trimethoprim, micanazole, and nystatin were
used as positive controls against both bacteria and yeast in the disk
diffusion method. The results of the antibacterial and antifungal
studies of all the synthesized compounds and those of the antibiotics
are depicted in Table 3.
Hsalbsmh and its Pd, Pt complexes were effective against all the
gram-positive, gram-negative bacteria and fungi.
The presence of electron densities in the \SO2NH\ group of
sulfonamides contributes positively to the increase of the activity of
the ligand against tested bacteria [33], but a decrease in electron
densities by the coordination of donor atoms caused a decrease of
activity [34]. Perhaps for this reason the nickel complex displayed
good activity against gram-negative bacteria but the Co complex
displayed poor activity against gram-positive bacteria, and the Cu
complex displayed no activity against any bacteria or fungi. When
these complexes were compared with each other, the Pd and Pt
complexes displayed more activity than the Ni and Co complexes. The
Cu complex displayed no activity against the tested bacteria.
Conclusions
In conclusion, a series of novel aromatic sulfonamide complexes
were synthesized and their antimicrobial activities were evaluated.
All compounds demonstrated potent inhibition against all the strains
tested. From the spectroscopic characterization, it was concluded that
sulfonylhydrazones act as bidentate ligands, coordinating through
\C_N and phenolic \OH via deprotonation. Further research in this
area is in progress at our laboratory. Consequently, these compounds
may be recommended for industrial application.
Acknowledgments
The authors are grateful to the TUBITAK Research Foundation for
its financial support under project number 104 T 390.
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