Synthesis, antibacterial and lipoxygenase activities of N-[(dimethyl substituted)phenyl]-N-(4-chlorophenyl)-4-chlorobenzenesulfonamides

Article abstract of DOI:10.14233/ajchem.2015.17431

In present research work, a new series of N-[(dimethyl substituted)phenyl]-N-(4-chlorophenyl)-4-chlorobenzenesulfonamides (5a-f) was synthesized and also evaluated for their biological activities. The reaction of 4-chlorobenzenesulfonyl chloride (1) with dimethyl substituted aniline (2a-f) in aqueous alkaline medium yielded N-[(dimethyl substituted)phenyl]-4-chlorobenzenesulfonamides (3a-f). The target compounds 5a-f were synthesized by reacting the compounds 3a-f with electrophile, 4-chlorobenzyl chloride (4) in aprotic solvent, DMF and NaH. All the synthesized compounds were characterized by IR, ¹H NMR and EIMS. All the synthesized derivatives were screened for antibacterial potential and were also subjected for lipoxygenase enzyme inhibition activity.

Full text of DOI:10.14233/ajchem.2015.17431

Asian Journal of Chemistry; Vol. 27, No. 5 (2015), 1647-1650
A
SIAN
J
OURNAL OF HEMISTRY
C
http://dx.doi.org/10.14233/ajchem.2015.17431
Synthesis, Antibacterial and Lipoxygenase Activities of
N-[(Dimethyl substituted)phenyl]-N-(4-chlorophenyl)-4-chlorobenzenesulfonamides
1,*
1
1
1
1
AZIZ-UR-REHMAN , IMRAN AHMAD , M. ATHAR ABBASI , KHADIJA NAFEESA , SABAHAT Z. SIDDIQUI ,
1
2
3
3
GHULAM HUSSAIN , JAMEEL RAHMAN , IRSHAD AHMED and SAIRA AFZAL
1Department of Chemistry, Government College University, Lahore-54000, Pakistan
2Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan
3Department of Pharmacy, Faculty of Pharmacy and Alternative Medicine, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan
*Corresponding author: Tel: +92 42 111000010, Ext: 449; E-mail: azizryk@yahoo.com
Received: 20 February 2014;
Accepted: 6 May 2014;
Published online: 20 February 2015;
AJC-16861
In present research work, a new series of N-[(dimethyl substituted)phenyl]-N-(4-chlorophenyl)-4-chlorobenzenesulfonamides (5a-f) was
synthesized and also evaluated for their biological activities. The reaction of 4-chlorobenzenesulfonyl chloride (1) with dimethyl substituted
aniline (2a-f) in aqueous alkaline medium yielded N-[(dimethyl substituted)phenyl]-4-chlorobenzenesulfonamides (3a-f). The target
compounds 5a-f were synthesized by reacting the compounds 3a-f with electrophile, 4-chlorobenzyl chloride (4) in aprotic solvent, DMF
and NaH. All the synthesized compounds were characterized by IR, 1H NMR and EIMS. All the synthesized derivatives were screened for
antibacterial potential and were also subjected for lipoxygenase enzyme inhibition activity.
Keywords: Dimethyl substituted aniline, Sulfonamides, Antibacterial activity, Lipoxygenase activity, Spectral analysis.
meters at 500 MHz using tetramethylsilane as reference standard
and chemical shift mentioned in δ-values while the coupling
constants (J) are mentioned in Hz. JMS-HX-110 spectrometer
was used to record the mass spectra (EIMS).
INTRODUCTION
Sulfonamides is a class of organic compounds that exhibit
sulfamoyl group (-NSO2) as a functional group. Sulfonamides
are known for their high biological potential and medicinal
importance. Due to excellent biological activities, sulfonamides
are widely used as antimicrobial, anticancer, anti-inflammatory
and antiviral agents1-5. Sulfonamides have been subjected to a
number of biological evaluations like antifungal and enzyme
inhibitory potential6,7.
Procedure for the synthesis of N-[(dimethyl substituted)
phenyl]-4-chlorobenzene-sulfonamides (3a-f): Dimethyl
substituted aniline (2a-f, 0.01 mol) was suspended in 30 mL
distilled water in a 100 mL round bottom flask and then added
Na2CO3 solution (20 %) to maintained the pH 9-10.Afterward,
4-chlorobenzenesulfonyl chlorides (1, 0.01 mol) was
introduced into the flask slowly with continuous stirring. The
reaction contents were allowed to stir for 2-3 h and reaction
progress was monitored by TLC till the single spot. On reaction
completion dilute HCl was added along with continuous
shaking to bring the pH to 3-4. The precipitates of compounds
3a-f formed were then filtered, washed, dried and followed
the further reaction.
In continuation of our interest8-11, we have described herein
the synthesis of various N-substituted sulfonamides derived
from dimethyl substituted aniline and reported their biological
activities. The newly synthesized compounds showed varying
degree of antibacterial and lipoxygenase activities.
EXPERIMENTAL
Thin layer chromatography (TLC) was utilized to detect
the purity of the synthesized compounds using EtOAc and
n-hexane as mobile phase and visualized by UV lamp at 254
nm. Griffin-George melting point apparatus was used to record
the melting points of all derivatives by open capillary tube
method and were found uncorrected. Jasco-320-A spectro-
photometer was utilized for IR spectra by KBr pellet method.
1H NMR spectra were recorded in CD3OD on a Bruker spectro-
Synthesis of N-[(dimethyl substitu-ted)phenyl]-N-(4-
chlorophenyl)-4-chlorobenzene-sulfonamides (5a-f): Com-
pounds 3a-f (0.01 mol) was dissolved in 10 mL N,N-dimethyl
formamide (DMF) in a 100 mL round bottom flask. Sodium
hydride (0.01 mol) was added to reaction flask and set to stir
for 0.5 h at room temperature. The electrophile, 4-chlorobenzyl
chloride (4, 0.01 mol) were added to reaction contents and set
to stir for 4-5 h. to synthesize the target compounds 5a-f. On

1648 Aziz-ur-Rehman et al.
Asian J. Chem.
reaction completion, the reaction mixture was quenched with
ice cold distilled water. The precipitates formed were then
filtered, washed with distilled water and dried to yield the target
compounds 5a-f.
N-(3,4-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5e):Yellow amorphous solid;
yield: 86 %; m.p. 120-122 °C; mol. formula: C21H19Cl2NSO2;
mol. wt.: 420; IR (KBr, νmax, cm-1): 3058 (Ar-H), 1534 (Ar
C=C), 1415 (-SO2-), 1146 (C-N), 567 (C-Cl); 1H NMR (500
MHz, CD3OD, ppm): δ 7.65 (d, J = 9.0 Hz, 2H, H-2', H-6'),
7.46 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.21 (d, J = 8.5 Hz, 2H,
H-2", H-6"), 7.05 (d, J = 8.5 Hz, 2H, H-3", H-5"), 6.96 (d, J =
13.0 Hz, 1H, H-6), 6.84 (br. s, 1H, H-2), 6.79 (dd, J = 10.0,
1.0 Hz, 1H, H-5), 4.17 (s, 2H, H-7"), 2.16 (s, 6H, CH3-3, CH3-
4); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+, 175 [C6H4ClSO2]+,
245 [M-C6H4ClSO2]+, 120 [M-C13H9Cl2SO2]+, 111 [C6H4Cl]+,
105 [M-C13H10Cl2NSO2]•+, 90 [M-C14H13ClNSO2]+, 76 [C6H4]•+,
75 [M-C15H16ClNSO2]•+.
N-(2,3-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5a): White amorphous solid;
yield: 81 %; m.p. 122-124 °C; mol. formula: C21H19Cl2NSO2;
mol. wt.: 420; IR (KBr, νmax, cm-1): 3057 (Ar-H), 1533 (Ar
C=C), 1413 (-SO2-), 1142 (C-N), 563 (C-Cl); 1H NMR (500
MHz, CD3OD, ppm): δ 7.63 (d, J = 9.0 Hz, 2H, H-2', H-6'),
7.48 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.18 (d, J = 8.5 Hz, 2H,
H-2", H-6"), 7.03 (d, J = 8.5 Hz, 2H, H-3", H-5"), 7.04 (d, J =
7.5 Hz, 1H, H-6), 6.94 (t, J = 7.5 Hz, 1H, H-5), 6.77 (d, J =
8.0 Hz, 1H, H-4), 4.25 (s, 2H, H-7"), 2.21 (s, 3H, CH3-2),
1.98 (s, 3H, CH3-3); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+,
175 [C6H4ClSO2]+, 245 [M-C6H4ClSO2]+, 120 [M-
C13H9Cl2SO2]+, 111 [C6H4Cl]+, 105 [M-C13H10Cl2NSO2]•+, 90
[M-C14H13ClNSO2]+, 76 [C6H4]•+, 75[M-C15H16ClNSO2] •+.
N-(2,4-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5b): Light grey amorphous
solid; yield: 83 %; m.p. 120-122 °C; mol. formula: C21H19Cl2N-
SO2; mol. wt.: 420; IR (KBr, νmax, cm-1): 3056 (Ar-H), 1527
N-(3,5-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5f): Light yellow amorphous
solid; yield: 84 %; m.p. 122-124 °C; mol. formula: C21H19Cl2N-
SO2; mol. wt.: 420; IR (KBr, νmax, cm-1): 3055 (Ar-H), 1532
1
(Ar C=C), 1414 (-SO2-), 1139 (C-N), 564 (C-Cl); H NMR
(500 MHz, CD3OD, ppm): δ 7.63 (d, J = 9.0 Hz, 2H, H-2', H-
6'), 7.43 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.23 (d, J = 8.5 Hz,
2H, H-2", H-6"), 7.16 (d, J = 8.5 Hz, 2H, H-3", H-5"), 6.73 (s,
2H, H-2, H-6), 6.66 (s, 1H, H-4), 4.18 (s, 2H, H-7"), 2.19 (s,
6H, CH3-3, CH3-5); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+,
175 [C6H4ClSO2]+, 245 [M-C6H4ClSO2]+, 120 [M-C13H9Cl2SO2]+,
111 [C6H4Cl]+, 105 [M-C13H10Cl2NSO2]•+, 90 [M-C14H13ClNSO2]+,
76 [C6H4]•+, 75 [M-C15H16ClNSO2]•+.
1
(Ar C=C), 1412 (-SO2-), 1142 (C-N), 557 (C-Cl); H NMR
(500 MHz, CD3OD, ppm): δ 7.63 (d, J = 8.5 Hz, 2H, H-2', H-
6'), 7.46 (d, J = 9.0 Hz, 2H, H-3', H-5'), 7.17 (d, J = 8.5 Hz,
2H, H-2", H-6"), 7.07 (d, J = 8.5 Hz, 2H, H-3", H-5"), 6.93
(br. s, 1H, H-6), 6.89(dd, J = 6.0,1.5 Hz, 1H, H-5), 6.85 (s,
1H, H-3), 4.23 (s, 2H, H-7"), 2.24 (s, 3H, CH3-2), 1.98 (s, 3H,
CH3-4); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+, 175
[C6H4ClSO2]+, 245 [M-C6H4ClSO2]+, 120 [M-C13H9Cl2SO2]+,
111 [C6H4Cl]+, 105 [M-C13H10Cl2NSO2]•+, 90 [M-C14H13ClN-
SO2]+, 76 [C6H4]•+, 75 [M-C15H16ClNSO2]•+.
N-(2,5-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5c): White amorphous solid;
yield: 86 %; m.p. 110-112 °C; mol. formula: C21H19Cl2NSO2;
mol. wt.: 420; IR (KBr, νmax, cm-1): 3058 (Ar-H), 1532 (Ar
C=C), 1410 (-SO2-), 1139 (C-N), 557 (C-Cl); 1H NMR (500
MHz, CD3OD, ppm): δ 7.63 (d, J = 9.0 Hz, 2H, H-2', H-6'),
7.45 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.13 (d, J = 8.5 Hz, 2H,
H-2", H-6"), 7.09 (d, J = 8.5 Hz, 2H, H-3", H-5"),6.95 (d, J =
7.5 Hz, 1H, H-3), 6.91 (d, J = 8.0 Hz, 1H, H-4), 6.84 (s, 1H,
H-6), 4.21 (s, 2H, H-7"), 2.17 (s, 3H, CH3-2), 1.91 (s, 3H,
CH3-5); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+, 175
[C6H4ClSO2]+, 245 [M-C6H4ClSO2]+, 120 [M-C13H9Cl2SO2]+,
111 [C6H4Cl]+, 105 [M-C13H10Cl2NSO2]•+, 90 [M-C14H13ClN-
SO2]+, 76 [C6H4]•+, 75 [M-C15H16ClNSO2]•+.
N-(2,6-Dimethylphenyl)-N-[(4-chlorophenyl)methyl]-
4-chlorobenzenesulfonamide (5d): Cream white amorphous
solid; yield: 87%; m.p. 128-130 °C; mol. formula:
C21H19Cl2NSO2; mol. wt.: 420; IR (KBr, νmax, cm-1): 3054 (Ar-
H), 1532 (Ar C=C), 1407 (-SO2-), 1139 (C-N), 553 (C-Cl); 1H
NMR (500 MHz, CD3OD, ppm): δ 7.68 (d, J = 9.0 Hz, 2H, H-
2', H-6'), 7.51 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.15 (d, J = 8.5
Hz, 2H, H-2", H-6"), 7.11 (d, J = 8.5 Hz, 2H, H-3", H-5"),
7.06-6.96 (m, 3H, H-3 to H-5), 4.19 (s, 2H, H-7"), 2.02 (s,
6H, CH3-2, CH3-6); EIMS (m/z): 420 [M]•+, 356 [M-SO2]•+,
175 [C6H4ClSO2]+, 245 [M-C6H4ClSO2]+, 120 [M-
C13H9Cl2SO2]+, 111 [C6H4Cl]+, 105 [M-C13H10Cl2NSO2]•+, 90
[M-C14H13ClNSO2]+.
Antibacterial activity: The antibacterial activity method
was based on the principle that microbial cell number or microbial
growth was directly related to the log phase of growth with
increase in absorbance of broth medium12,13
.
Lipoxygenase assay: Lipoxygenase activity was assayed
according to the reported method14-16 but with slight modi-
fications.
Statistical analysis:All the measurements were accounted
in triplicate and statistical analysis was performed by Microsoft
Excel 2010. Results are presented as mean SEM.
RESULTS AND DISCUSSION
The undertaken research work was an effort to synthesize
a new series of biological active compounds which may be helpful
in drug development program. The parent molecules, N-
[(dimethyl substituted)phenyl]-4-chlorobenzene-sulfonamide
(3a-f) were synthesized by coupling dimethyl substituted
aniline (2a-f) with 4-chlorobenzenesulfonyl chlorides (1) in
basic aqueous medium under dynamic pH control. The
products were obtained on acidification by dil. HCl drop by
drop but avoid excess of acid that can decrement the yield.
The parent molecules were derivatized by gearing up with
electrophile, 4-chlorobenzyl chloride (4) to synthesize the
target compounds 5a-f (Scheme-I) in the presence of NaH as
activator in a polar aprotic solvent. The structures of all the
synthesized derivatives were corroborated by spectral data.
Compound 5a was precipitated as white amorphous solid
with 81 % yield and having melting point 122-124 °C. The
EI-MS spectrum showed the molecular ion peak at m/z 248-
[M]+• owing to molecular formula as C21H19NSO2Cl2. In the
aromatic region of 1H NMR spectrum, the downfield signals
appeared at δ 7.63 (d, J = 9.0 Hz, 2H, H-2', H-6') and 7.48

Vol. 27, No. 5 (2015)
Synthesis of N-[(Dimethyl substituted)phenyl]-N-(4-chlorophenyl)-4-chlorobenzenesulfonamides 1649
R1
as N-(2,3-dimethylphenyl)-N-[(4-chloro-phenyl)-methyl]-4-
O
O
O
O
chlorobenzene sulfonamide. Similarly the structures of other
synthesized molecules were corroborated on the basis of
spectral evidences of IR, 1H NMR and EI-MS.
R2
Aq. Na2CO3,
pH = 9-10
R1
R2
S
S
Cl
N
H2N
H
+
Stirring at RT
Cl
Cl
3a-f
1
2a-f
Antibacterial activity (in vitro): The percentage inhibi-
tion and MIC values of the synthesized molecules relative to
ciprofloxacin are shown in Tables 1 and 2, respectively.Among
the synthesized compounds, the compound 5f was the most
active inhibitor against P. aeruginosa with MIC value of 13.11
0.96 µM relative to the reference standard having MIC value
of 8.48 1.91 µM, probably due to the presence of 3,5-disubs-
tituted phenyl group present in the molecule. Against E. coli
and S. typhi, the compound 5f showed promising activity with
MIC value 13.76 0.49 and 19.04 0.79 µM relative to the
reference standard drug having MIC value 8.06 1.07 and
9.27 1.58 µM, respectively. In general the activity expressed
by the synthesized compounds was good as supported by their
MIC values.
CH2
DMF, NaH
Stirring at RT
Cl
O
Cl
R1
4
3
O
1
R2
5
S
N
3'
1'
7''
5'
H2C
Cl
1''
3''
5''
5a-f
Cl
Compound
5a
5b
5c
5d
5e
5f
2-CH3 2-CH3 2-CH3 2-CH3 3-CH3 3-CH3
3-CH3 4-CH3 5-CH3 6-CH3 4-CH3 5-CH3
R1
R2
Scheme-I:Outline for the synthesis of N-[(dimethyl substituted)phenyl]-N-
(4-chlorophenyl)-4-chlorobenzenesulfonamides
Enzyme inhibition activity: The screening against
lipoxygenase (LOX) enzyme revealed that these molecules
exhibited good inhibitory potential as it was evident from their
IC50 values (Table-3). The compounds, 5a and 5b were the
relatively good inhibitor having IC50 values of 87.92 1.38
and 95.57 1.35 µmol, respectively, relative to Baicalein, a
reference standard with IC50 value of 22.4 1.3 µmol. The
inhibitory results showed that the compounds could be
potential target in the drug discovery and drug development
program.
(d, J = 8.5 Hz, 2H, H-3', H-5'), due to double integration and
higher coupling constant, these signals were assigned to the
protons of 2-chlorobenzenesulfonyl group and the signals at δ
7.18 (d, J = 8.5 Hz, 2H, H-2", H-6"), 7.03 (d, J = 8.5 Hz, 2H,
H-3", H-5") and 4.25 (s, 2H, H-7") affirmed the presence of
4-chlorobenzyl moiety. The other three signals of aromatic
region resonating at 7.04 (d, J = 7.5 Hz, 1H, H-6), 6.94 (t, J =
7.5 Hz, 1H, H-5), 6.77 (d, J = 8.0 Hz, 1H, H-4) which indicated
the presence of tri-substituted aromatic ring. In the aliphatic
region the signals of two methyl group were appeared at δ
2.21 (s, 3H, CH3-2) and 1.98 (s, 3H, CH3-3). All the functional
groups in the molecule were supported by IR and the EI-MS
spectral data. All these evidences assigned the structure of 5a
Conclusion
All the structures were elucidated through spectral analysis
and were supported by the biological screening. The results
TABLE-1
ANTIBACTERIAL ACTIVITY (%) INHIBITION) OF TESTED COMPOUNDS
(%) Inhibition
Compdound
Gram-negative bacteria
Gram-positive bacteria
S. typhi (-)
44.33 1.21
30.13 2.67
41.10 1.31
38.75 2.01
42.52 3.08
51.25 1.50
91.21 0.22
E. coli (-)
K. pneumoniae (-) P. aeroginosa (-)
B. subtilis (+)
S. aerus (+)
44.35 1.19
34.87 4.13
44.63 4.22
47.35 0.88
43.95 2.51
48.42 0.96
91.98 0.04
44.54 3.61
28.01 3.63
33.97 3.30
56.86 1.52
31.81 4.48
66.81 1.52
92.00 0.23
30.64 1.09
32.70 2.41
47.10 1.81
40.23 1.68
42.80 3.11
34.14 1.95
90.63 0.12
49.79 2.04
36.23 0.59
55.27 2.27
62.25 3.42
58.55 3.27
61.38 1.04
91.38 0.01
49.75 3.45
33.46 4.84
50.97 4.91
51.05 3.15
39.89 2.27
55.10 0.20
90.35 0.21
5a
5b
5c
5d
5e
5f
Ciprofloxacin
TABLE-2
ANTIBACTERIAL ACTIVITY (MIC) OF THE TESTED COMPOUNDS
MIC
Compdound
Gram-negative bacteria
Gram-positive bacteria
S. typhi (-)
E. coli (-)
K. pneumoniae (-) P. aeroginosa (-)
B. subtilis (+)
S. aerus (+)
-
-
-
-
-
-
5a
-
-
-
-
-
-
5b
-
-
-
-
-
-
-
-
15.62 1.27
15.35 2.21
18.07 0.62
13.11 0.96
8.48 1.91
19.48 1.91
19.07 0.65
-
17.04 0.80
9.04 1.86
-
-
-
-
5c
5d
5e
5f
17.67 1.31
-
13.76 0.49
8.06 1.07
19.04 0.79
9.27 1.58
Ciprofloxacin
8.51 0.14
8.95 1.33
Note: Minimum inhibitory concentration (MIC) was measured with suitable dilutions (5-30 µg/well) and results were calculated using EZ-Fit
Perrella Scientific Inc. Amherst USA software

1650 Aziz-ur-Rehman et al.
Asian J. Chem.
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TABLE-3
LIPOXYGENASE ACTIVITY OF TESTED COMPOUNDS
LOX
Compound
Conc. (mM)
0.25
(%) Inhibition
97.87 1.21
96.98 1.25
33.45 1.19
52.36 1.14
45.36 1.21
80.09 1.11
93.79 1.27
IC50
87.92 1.38
95.57 1.35
-
196.21 1.16
-
5a
5b
5c
5d
5e
0.25
0.25
0.25
0.25
0.25
0.5
9. H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, K.M. Khan, Int. J. Pharm.
Pharm. Sci., 4, 443 (2012).
113.95 1.29
22.4 1.3
5f
10. H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, R. Hussain, K.M. Khan, M.
Ashraf, S.A. Ejaz and M.Q. Fatmi, Turkish J. Chem., 38, 189 (2014).
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14. H.C. Clapp, A. Banerjee and S.A. Rotenberg, J. Biochem., 24, 1826
(1985).
Baicalein
of biological analysis, obtained as MIC and IC50 values rendered
the synthesized compounds as moderate inhibitors for enzymes
but relatively better antibacterial agents.
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