Synthesis, characterization and biological activities of 2-[(methyl sulfonyl)]amino benzoic acid derivatives and their metal complexes

Article abstract of DOI:10.14233/ajchem.2015.17807

Sulfonamide derivatives and their metal complexes are acknowledged pharmaceutical moieties because this group has been played the key role as a functional part of the most of the drug structures due to constancy and for bearance in human beings. Sulfonamides have endowed great biological potential such as antibacterial, insulin releasing, carbonic anhydrase inhibitory, anti-inflammatory, antifungal and antitumor activities. In the present work, 2-[(methyl sulfonyl)] amino benzoic acid was N-alkylated using alkylating agent such as methyl. Due to the presence of electron donating groups like, -COOH, -SO₂, N-, the above mentioned molecules act as an excellent chelating agent. These substituted N-alkylated sulfonamide ligands were treated with a number of outer and inner transition metals such as Co(II), Cu(II), Ce(II), Pr(II), Dy(II) and Nd(II) to form coordinate complexes. These newly synthesized sulfonamides and their metal complexes were characterized by melting points, solubility, colour, FTIR analysis and XRD. These products were subjected for antimicrobial activities as well as other accessible applications.

Full text of DOI:10.14233/ajchem.2015.17807

Asian Journal of Chemistry; Vol. 27, No. 4 (2015), 1326-1330
A
SIAN
J
OURNAL OF HEMISTRY
C
http://dx.doi.org/10.14233/ajchem.2015.17807
Synthesis, Characterization and Biological Activities of
2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes
1,*
1
1
1
1
TANVEER HUSSAIN BOKHARI , NAVEEDA ASHRAF , MUHAMMAD SHAFIQ , MATLOOB AHMED , NASIR RASOOL ,
2
3
4
5
HAZOOR AHMAD SHAD , NABEELA ASHRAF , NADEEM ARSHAD and MUHAMMAD NAWAZ TAHIR
1Department of Chemistry, Government College University, Faisalabad-38000, Pakistan
2Department of Chemistry, University of Sargodha-60800, Pakistan
3Department of Applied Chemistry, UET, Lahore-54890, Pakistan
4Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, Kingdom of Saudi Arabia
5Department of Physics, University of Sargodha-60800, Pakistan
*Corresponding author: E-mail: tanveer.bokhari@yahoo.com
Received: 12 April 2014;
Accepted: 2 June 2014;
Published online: 4 February 2015;
AJC-16784
Sulfonamide derivatives and their metal complexes are acknowledged pharmaceutical moieties because this group has been played the
key role as a functional part of the most of the drug structures due to constancy and for bearance in human beings. Sulfonamides have
endowed great biological potential such as antibacterial, insulin releasing, carbonic anhydrase inhibitory, anti-inflammatory, antifungal
and antitumor activities. In the present work, 2-[(methyl sulfonyl)] amino benzoic acid was N-alkylated using alkylating agent such as
methyl. Due to the presence of electron donating groups like, -COOH, -SO2, N-, the above mentioned molecules act as an excellent
chelating agent. These substituted N-alkylated sulfonamide ligands were treated with a number of outer and inner transition metals such
as Co(II), Cu(II), Ce(II), Pr(II), Dy(II) and Nd(II) to form coordinate complexes. These newly synthesized sulfonamides and their metal
complexes were characterized by melting points, solubility, colour, FTIR analysis and XRD. These products were subjected for antimicrobial
activities as well as other accessible applications.
Keywords: Sulfonamide derivatives, Pharmaceutical agent, Antibacterial, Antifungal.
can often be boosted19 up by coordination with suitable metal
ions. In pharmacology, the activity has been found to be highly
INTRODUCTION
The transition metal complexes have gained attention of
dependent on the identity of the donor sequence of the ligands,
inorganic, metallo-organic as well as bio-organic chemists
because different ligands show broadly different biological
because of their extensive applications in wide ranging areas
activities although they may differ only slightly in their
from material science to biological sciences1. Sulfonamide
molecular structure20. There is a real perceived need for the
molecules have gained attention in pharmaceutical and agricul-
discovery of new compounds having strong antimicrobial
tural areas2 because of their extensive biological activities3.
activities. Sulfonamides and their metal complexes are known
Metal complexes of sulfonamides are extensively studied due
to be biologically significant and attractive because of their
to synthetic flexibility, selectivity and sensitivity towards a
properties such as antidiabetic, antiinflammatory, antibacterial
variety of metal atoms4. Some of them are also used as organic
and antifungal21,22
.
compounds. These are used in the treatment of toxoplasmosis,
nocardiasis, urinary tract infections, trachoma, chancroid,
malaria, meningitis, streptococcal pharyngitis, bacillary dysen-
tery and conjunctivitis5-7.A number of biological activities have
been played by sulfonamide drugs such as antibacterial8
antiinflammatory9 carbonic anhydrase inhibitory10-12 insulin
releasing13,14 and antitumor15 activities16. Other available
commercial drugs, having sulfonamide structure, are the
antihypertensive agents like antiviral HIV protease inhibitor17
and bosentan18. The various organic therapeutic agents'worth
Compounds of benzoic acid derivative play an important
role in many bio-chemical reactions23,24. The copper(II),
cobalt(II), cerium(II), praseodymium(II), dysprosium(II) and
neodymium(II) complexes of sulfonamide ligands have played
a vital role in the development of coordination chemistry25. In
view of the above considerations, we have synthesized and
characterized Co(II), Cu(II), Ce(II), Pr(II), Dy(II) and Nd(II)
complexes of sulfonamide derivatives and studied the
biological activity of these complexes.

Vol. 27, No. 4 (2015)
Synthesis of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes 1327
O
Main objectives of the present research work were, to
develop reaction conditions for the successful synthesis of
different kinds of derivatives of 2-[(methyl sulfonyl)amino]-
benzoic acid and to check whether the new lead compounds
were biologically active or not.
O
C
C
OH
O
OMe
O
HCl
H2O
+NaOH
S
CH3
N
H
S
CH3
N
H
O
O
EXPERIMENTAL
Scheme-II
All the commercially available reagents and chemicals
were used as such without further purification for the prepara-
tion of ligands and metal complexes.All organic solvents were
purchased from Merck. The IR spectra were recorded of
(Thermo Nicolet FT-IR, Nicolet-200, USA) spectrometer in
the 4000-400 cm–1 region using KBr pellets. A verity of glass-
ware's were used which were oven and flame dried. The
progress and completion of reactions was monitored by thin-
layer chromatography. UV light at 254 nm was used to visua-
lize the chromatograms. Melting points were determined
in open capillary tubes on an electrothermal (Griffin 1090)
melting point.
wise addition of the mixture of methyl-2-amino-5-bromoben-
zoate (0.9 mL) and dichloromethane (10 mL) in it. The reaction
mixture was stirred for 3.5 h (at room temperature) keeping
the pH of the mixture alkaline (8-12) by adding triethylamine.
After completion of reaction, the mixture was neutralised with
the help of dilute hydrochloric acid. The separated organic
layer was dried by using sodium sulphate and removed under
vacuum (11 torr) to get yellow crude solid which gave white
crystalline product after recrystallization from ethanol26
(Scheme-III).
O
O
Synthesis of 2-[(methyl sulfonyl)]amino benzoic acid
(L1): It followed two step preparations. First step involved the
conversion of methyl anthranilate to 2-[(methyl sulfonyl)]-
amino benzoate. For this purpose, solution of methanesulfonyl
chloride (0.8 mL) in dichloromethane (10 mL) was added to
methyl anthranilate (0.9 mL) over 15-20 min at room tempe-
rature. The reaction mixture was stirred for 3.5 h (at room
temperature) and maintained the pH of the mixture alkaline
(8-12) by adding triethylamine. After complete conversion of
reactant, the reaction mixture was neutralized with dilute
hydrochloric acid. The separated organic layer was dried Na2SO4
and removed under vacuum (11 torr) to get yellow crude solid
which gave white crystalline product after recrystallization
from ethanol26 (Scheme-I).
C
OCH3
O
Br
C
OCH3
+ Cl-SO2-CH3
Br
Dicholoromethane
Triethylamine
S
N
H
CH3
N
H
H
O
methyl 2-amino-5-bromobenzoate
methyl 5-bromo-2-
(methylsulfonamido)benzoate
Scheme-III
This step involved the N-alkylation. Methyl 5-bromo-2-
(methyl sulfonamido)benzoate (33 mmol) was dissolved in
DMF (10 mL) and added to n-hexane washed suspension of
NaH (66 mmol) in DMF (10 mL).After stirring the suspension
for 45 min, alkyl iodide was added (66 mmol) and the resulting
mixture was stirred at room temperature for 12-16 h. TLC (n-
hexane:ethyl acetate in 4:1 ratio) was used to monitor the
progress of reaction. The mixture was poured into cold 3 N
hydrochloric acid and potassium carbonate was used to neutra-
lize the pH. The resultant mixture was extracted with ethyl
acetate and the combined organic layers were dried over K2SO4
and evaporated under reduced pressure to get methyl 5-bromo-
2-(N-methyl methylsulfonamido)benzoate27 (Scheme-IV).
O
O
C
OCH3
O
C
OCH3
H
O
Dichloromethane
Triethylamine
+
Cl-S-CH3
O
N
H
S
CH3
N
H
O
Scheme-I
O
C
O
C
This involved the preparation of 2-[(methyl sulfonyl)]
amino benzoic acid by the addition of the mixture of 2-[(methyl
sulfonyl)amino]benzoate (0.446 g, 1.930 mmol) and sodium
hydroxide (0.083 g, 2.075 mmol) in aqueous media (10 mL
distilled water) in a round bottom flask and stirred at room
temperature for 7 h with the appearance of light yellow colour
precipitates then stirred at 50 to 60 °C temperature for 2 h
followed by addition of dilute hydrochloric acid until the
appearance of off white precipitates. Then precipitates were
filtered, washed with cold water and dried under vacuum
followed by recrystallization in ethanol27 (Scheme-II).
Synthesis of 5-bromo-2-(N-methyl sulfonamido)-
benzoic acid (L2): It was synthesized in three steps i.e., the
N-sulfonation, N-alkylation and simple hydrolysis.
Br
OCH3
O
OCH3
Br
CH3I
DMF
O
+
NaH
S
N
S
CH3
N
H
CH3
O
O
CH3
methyl 5-bromo-2-
(methylsulfonamido)benzoate
methyl 5-bromo-2-(
N-
methylmethylsulfonamido)benzoate
Scheme-IV
In third step involved the hydrolysis of methyl 5-bromo-
2-(N-methyl methyl sulfonamido)benzoate. For this, the
mixture of methyl 5-bromo-2-(N-methyl methyl sulfona-
mido)benzoate (0.446 g, 1.38 mmol) and sodium hydroxide
(0.083 g, 2.075 mmoles) was added in aqueous media (10 mL
distilled water) in a round bottom flask and stirred at room
temperature for 7 h until the appearance of light yellow preci-
pitates then refluxed it for 2 h followed by addition of dilute
In 1st step, solution of methanesulfonyl chloride (8 mL)
in dichloromethane (10 mL) was taken in round bottom flask
and stirred it for 15-20 min at room temperature with the drop

1328 Bokhari et al.
Asian J. Chem.
O
C
hydrochloric acid until the appearance of brownish yellow
precipitates. The progress of reaction was monitored by TLC
(n-hexane:ethyl acetate in 4:0.75 ratios). After completion of
reaction; precipitates were filtered, washed with cold water and
dried under vacuum followed by recrystallization in ethanol
(Scheme-V).
OH
O
MeOH
reflux
+
MX
S
CH3
N
R
O
CH3
O
O
S
N
O
C
O
C
R
OCH3
O
OH
O
Br
O
C
Br
HCl
O
+ NaOH
Aqueous media
N
S
CH3
N
S
CH3
M
O
O
CH3
CH3
C
O
Methyl 5-bromo-2-(N-
methylmethylsulfonamido)benzoate
5-Bromo-2-(N-methylmethyl-
sulfonamido)benzoate
O
N
Scheme-V
R
S
O
O
Synthesis of metal complexes by sulfonamide ligands:
The metal complexes were synthesized by the following general
procdure, appropriate metal salt wasdissolved in methanol (7
mL) in 100 mL round bottom flask and stirred until the clarity
of the solution. Then to this solution, corresponding ligand
(L1, L2) (0.05 g) was added and refluxed it for 6 to 7 h for the
synthesis of L1M1, L1M2, L1M3 and L1M4 complexes while 5 to
46 h for L2M5 and L2M6 at a temperature of 50-60 °C. Metal to
ligand ratio was 0.5:1. Mixture appeared coloured. TLC was
performed to monitor the progress of reaction. Then mixture
was filtered and product was appeared in the filtrate on slow
evaporation by washing with ethanol (Scheme-VI).
CH3
Where M = Ce, Pr, Nd, Dy, Cu or Co and X = acetate, chloride or nitrates
Scheme-VI
Single crystal X-rays studies for 5-bromo-2-(N-methyl-
sulfonamido)benzoic acid: This compound consists of two
molecules in the crystallographic asymmetric unit which differs
from each other geometrically. The molecular structure of the
compound, 5-bromo-2-(N-methylsulfonamido)benzoic acid
with atom number arrangement is given in Fig. 1. The crystallo-
graphic data is shown in Table-3. In one molecule, the 4-
bromobenzoic acid moiety, group A (C1-C7/O1/O2/Br1) and
N-methylmethanesulfonamide, groups B (C8/C9/N1/S1/O3/
O4) are non-linear to each other and showed bond angle devia-
tion of 117.5(7)°. The dihedral angle between A/B groups is
87(1)°. The bond length (C4-Br1) in title molecule is 1.88(1),
which is little bit smaller than the bond length, 1.894(2) as
reported by Shafiq et al.27. All other bond lengths and angles
are approximately same as reported by Shafiq et al.27, with small
variation. In second molecule, both of the groups, C (C10-C16/
O5/O6/Br2) and N-methylmethanesulfonamide, D (C17/C18/
N2/S2/O7/O8) are shown approximately same deviation from
their planar behavior as exhibited by the first molecule, with
opposite direction. The dihedral angle between C and D is
-85(1)°. The bond length (C13-Br2) of second molecule is
slightly larger, 1.89(1) than the bond length 1.88(1) of first
RESULTS AND DISCUSSION
Two new bidentate sulfonamides, 2-[(methyl sulfonyl)]
amino benzoic acid and 5-bromo-2-[(N-methyl sulfonamido)]-
benzoic acid have been synthesized by N-sulfonation, N-
alkylation and simple hydrolysis of anthranilate and methyl-
2-amino-5-bromobenzoate, respectively. The metal complexes
of Cu(II), Co(II), Ce(II), Pr(II), Dy(II) and Nd(II) were
obtained by the reaction of metal chloride/acetate/nitrate with
bidentate ligand in 0.5:1 molar ratios. The physical data, shown
in Tables 1 and 2, of ligands and complexes, are consistent
with the proposed molecular formulae. Thecomplexesare of
bright colour and soluble in DMF, DMSO and other common
organic solvents like methanol, ethanol and ethyl acetate.
TABLE-1
PHYSICAL CHARACTERISTIC DATA OF SULFONAMIDE LIGANDS
Sulfonamide
ligands
Sulfonating agent
Amino benzoate
Physical state
Off white solid
Light yellowish brown
solid
m.f.
m.w. (g/mol) m.p. (oC)
L1
L2
Methyl sulfonylchloride Methyl anthranilate
Methyl sulfonylchloride Methy 2-amino-5-bromo
benzoate
C8H9O3NS
C9H10O4BrSN
215
308
186-189
143-147
TABLE-2
PHYSICAL CHARACTERISTICS DATA OF METAL COMPLEXES
Sulfonamide
ligands
Complex
Metal salt
Physical state
m.f.
m.w. (g/mol)
m.p. (°C)
L1M1
L1M2
L1M3
L1M4
L2M5
L2M6
L1
L1
L1
L1
L2
L2
Cerium nitrate
Praseodymium chloride Dark purple solid
Dysprosium nitrate
Neodymium chloride
Copper acetate
Dark purple solid
C16H18O8N2S2Ce
C16H18O8N2S2Pr
C16H18O8N2S2Dy
C16H18O8N2S2Nd
C18H18O8N2S2Br2Cu
C18H18O8N2S2Br2Co
566.0
567.0
588.5
570.0
677.5
673.0
184-188
143-147
168-172
89-94
> 300
> 300
Dark purple solid
Pinkish purple solid
Blackish green solid
Brownish black solid
Cobalt acetate

Vol. 27, No. 4 (2015)
Synthesis of 2-[(Methyl sulfonyl)]amino Benzoic Acid Derivatives and Their Metal Complexes 1329
not participate in bonding. The spectral bands, which are not
appeared in the ligand spectrum but appeared in the metal
complexes spectra within the range of 557.43, 522.71, 518.85,
522.71, 540.07 and 538.14 cm-1, corresponding to ν(M-N) and
435.43, 414.70, 422.41, 415.71, 424.34 and 451.34 cm-1 to
ν(M-O)28-30 vibrations, respectively. Appearance of ν(M-N)
and ν(M-O) vibrations indicates the involvement of N and O
atoms in complexation with metal ions under investigation.
Antibacterial activity: The antibacterial activity of the
synthesized ligand (L1, L2) and its complexes31 (L1M1), (L1M2),
(L1M3), (L1M4), (L2M5) and (L2M6) tested using agar diffusion
technique against Staphylococcus aureus, Bacillus subtilis,
Pasteurella multocida, Escherichia coli using streptomycin as
positive control32. Both ligands (L1, L2) showed the moderate
activity against the P. multocida and E. coli while the least
activity against the B. subtilis. In case of complexes, L2M5
complex was found to be highly active against all the bacterial
strains. L1M1, L1M2, L1M3 and L2M6 complexes exhibited
moderate activity against all the bacteria. While L1M4 showed the
least activity against Staphylococcus aureus and Bacillus subtilis.
Antifungal activity:The antifungal activity was performed
using fluconazole as positive control, against Aspergillus niger,
Aspergillus flavus, Helmenthosporium medis, Alternaria
alternate. Results are given in Table-4. Both ligands (L1, L2)
showed the moderate activity against the Helmenthosporium
medis and Alternaria alternate while the least activity against
the Aspergillus flavus. In case of complexes, L2M5 complex
was found to be highly active against all the fungal strains
especially against Aspergillus flavus. All the other complexes
exhibited moderate activity against all the bacteria, except L1M4
which showed the least activity against Aspergillus niger and
Aspergillus flavus.
Fig. 1. Single crystal X-ray structure of compound 5-bromo-2-(N-methyl-
sulfonamido)benzoic acid
TABLE-3
CRYSTAL STRUCTURE PARAMETERS FOR COMPOUND
5-BROMO-2-(N-METHYLSULFONAMIDO)BENZOIC ACID
Chemical formula C9H10BrNO4S
c(Å)
α(°)
β(°)
19.3428 (9)
Formula weight
Crystal system
Space group
a (Å)
308.15
Orthorhombic
Pna21
90
90
90
γ(°)
Cell volume
16.5633 (9)
2375.7 (2) Å3
molecule. Similarly, other bond lengths and angles are also
shown a small variation with respect to the first molecule.
Infrared spectroscopy: The infrared spectra of newly
formed ligands and their metal complexes were charactrized
as KBr pellets in the broad range of 4000-400 cm-1. These
spectra of sulfonamides and their metal complexes showed
remarkable broad bands as shown in Table-4. The values of
different vibrational frequencies were assigned to different
bonds by comparing spectra of ligands with the literature
values. The calculated IR bands of the Ce(II), Pr(II), Dy(II),
Nd(II), Cu(II), and Co(II), metal complexes are different from
their free ligand and provide significant indications regarding
the coordination and binding sites of the ligand to the metal
ion. The ν(C-O) vibrational mode for free ligand (L1, L2) was
observed at 1253.73, 1296.16 cm-1, shifted to 1166.93, 1172.72,
1166.93, 1166.08, 1068.56 and 1070.49 cm-1 in the spectra of
Ce(II), Pr(II), Dy(II), Nd(II), Cu(II) and Co(II) complexes of
metals respectively, indicating the coordination of carboxyl
oxygen to the metal. While the IR bands of ligands (L1, L2)
showed spectral peaks at 1338.10 and 1325.10 cm-1 which was
contributed to ν(C-N) vibration. In case of Ce(II), Pr(II), Dy(II),
Nd(II), Cu(II) and Co(II) complexes, this peak was shifted
slightly downwards to 1257.59, 1247.94, 1253.73, 1259.52,
1151.50 and 1151.50 cm-1, respectively, which indicate the
presence of ν(C-N) vibration and suggesting the participation
of amino nitrogen in complexation. Sulfonyl functional group
shows absorption bands at 1168.86 and 1157.29 cm-1 in the
spectra of free ligands (L1, L2) but showed slight shifts of
1028.06, 1031.92, 1022.27, 1037.70, 1336.67 and 1332.81
cm-1 in the complexes of Ce(II), Pr(II), Dy(II), Nd(II), Cu(II)
and Co(II), respectively, which indicate that this group does
TABLE-4
ANTIFUNGAL ACTIVITY OF SULFONAMIDE
LIGANDSAND THEIR METALCOMPLEXES
Fungal inhibition zone (mm)
Sample
Aspergillus Aspergillus Helmenthospo Alternaria
No.
niger
flavus
rium medis
alternate
L1
L2
L1M1
L1M2
L1M3
L1M4
L2M5
L2M6
13
13
15
14
12
11
22
11
12
12
13
14
13
10
25
12
14
16
11
12
13
15
23
12
27
13
14
13
13
12
13
24
13
Fluconazole
23
24
28
Minimum inhibitory concentration for antibacterial
activity: The minimum inhibitory concentration method was
used to investigate the efficacy of listed sulfonamides and metal
complexes against four bacteria S. aureus, B. subtilis, P. multocida,
E. coli by using streptomycin as positive control. These results
showed that the values of ligands and complexes were satisfying.
Results are summarized in Table-5.
Minimum inhibitory concentration for antifungal activity:
Ligands and their metal complexes efficacy was investigated
by using minimum inhibitory concentration method against
four fungal strains A. niger, A. flavus, G. lucidum, A. alternata

1330 Bokhari et al.
Asian J. Chem.
TABLE-5
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Minimum inhibitory concentration (µg/mL)
Sample No.
S. aureus B. subtilis
P. multocida
E. coli
250
225
250
248
262
285
115
251
57
3L1
3L2
3L1M1
3L1M2
3L1M3
3L1M4
3L2M5
3L2M6
265
251
224
225
250
285
124
262
74
262
262
249
234
251
276
28
285
255
278
265
251
224
125
250
274
98
Streptomycin
30
using fluconazole as positive control. These results were
helpful to conclude that the values of sulfonamides and their
complexes were satisfactory. Results are summarized in Table-6.
TABLE-6
MINIMUM INHIBITORY CONCENTRATION FOR
ANTIFUNGAL ACTIVITY OF SULFONAMIDE
LIGANDS AND THEIR COMPLEXES
Minimum inhibitory concentration (µg/mL)
Aspergillus Aspergillus Helmenthosporium Alternaria
Sample
No.
niger
261
260
215
250
275
285
151
284
130
flavus
275
275
261
251
260
301
115
275
125
medis
251
225
284
274
261
185
135
275
85
alternate
261
250
261
258
275
259
125
3L1
3L2
3L1M1
3L1M2
3L1M3
3L1M4
3L2M5
3L2M6
Fluconazole
260
75
Cytotoxicity: Sample's toxicity analysis was performed
and Statistix MINITAB 13 was used to obtain the results. The
significance of samples was compare with the help of two
standers. The erthrocytic membrane mechanical stability is a
good indicator for the screening of cytotoxicity. It is also depen-
dent upon their physical and structural properties. Haemolysis
is a infectious disease which occurs due to presence of parasites
(Plasmodium falciparum) and other microbes33. The given
figure showed the observed values of % haemolysis with selec-
ted values of ligands and complexes. On y-axis lysis of human
blood is compared. With the selected sample compounds on
x-axis comparing with positive control having (100 %) lysis.
While PBS used as a negative control have (0.0 %) lysis.
Samples showed good haemolytic activity by comparing them
with positive control. Results are summerized in Table-7.
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28. C. Tang, R. Tang, C. Tang and Z. Zeng, Bull. Korean Chem. Soc., 31,
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29. K. Nakamoto, IR and Raman Spectra of Inorganic and Coordination
Complexes, Part A: Theory and Applications in Inorganic Chemistry,
edn 5, Wiley, New York (1997).
30. M. Thomas, M.K.M. Nair and P.K. Radhakrishnan, Synth. React. Inorg.
Met-Org. Chem., 25, 471 (1995).
31. M.M.Ali, M.M.F. Ismail, M.S.A. El-Gaby, M.A. Zahran andY.A.Ammar,
Molecules, 5, 864 (2000).
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Qaisar, Afr. J. Pure Appl. Chem., 3, 71 (2009).
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TABLE-7
HAEMOLYTIC VALUES FOR SULFONAMIDE
LIGANDS AND THEIR COMPLEXES
Sample Hemolytic activity
Sample
No.
3L1M4
3L2M5
3L2M6
PBS
Hemolytic activity
(mean % S.D.)
No.
(mean % S.D.)
3.52 0.72
4.34 1.18
4.21 0.69
1.15 0.34
1.46 0.49
3L1
3L2
5.09 1.06
4.03 1.04
3.35 1.18
0.00 0.0
100 0.0
3L1M1
3L1M2
3L1M3
Triton (toxicity)