Synthesis of N-(un)substituted-N-(2-methoxyphenyl/phenyl)-4-chlorobenzenesulfonamides as potent antibacterial derivatives

Article abstract of DOI:10.14233/ajchem.2015.16704

Sulfonamides belong to a biologically dynamic class of compounds with considerable importance for organic synthetic chemists. In the presented work, a benign series of chlorinated sulfonamides, 3a-b, was synthesized by coupling alkoxy (un) substituted ani

Full text of DOI:10.14233/ajchem.2015.16704

Asian Journal of Chemistry; Vol. 27, No. 1 (2015), 71-74
ASIAN JOURNAL OF CHEMISTRY
http://dx.doi.org/10.14233/ajchem.2015.16704
Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-
Chlorobenzenesulfonamides as Potent Antibacterial Derivatives
1
,*
1
2
1
1
1
1
AZIZ-UR-REHMAN , M. ATHAR ABBASI , SOHAIL NADEEM , TAHIR RASHEED , NAEEM AHMED , MISBAH IRSHAD and KANIZ RUBAB
1
2
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Department of Chemistry, School of Science and Technology, University of Management and Technology, Lahore, Pakistan
*
Corresponding author: Tel: +92 42 111000010 Ext. 449; E-mail: azizryk@yahoo.com
Received: 16 November 2013; Accepted: 25 March 2014; Published online: 26 December 2014;
AJC-16508
Sulfonamides belong to a biologically dynamic class of compounds with considerable importance for organic synthetic chemists. In the
presented work, a benign series of chlorinated sulfonamides, 3a-b, was synthesized by coupling alkoxy (un) substituted anilines, 2a-b,
with 4-chlorobenzenesulfonyl chloride (1) under basic pH control in an aqueous medium. The sulfonamides, 3a-b, were geared up with
alkyl/aralkyl halides, 4-6, in a basic aprotic solvent to yield the target molecules, 7a-b, 8a-b and 9a-b. The structures of all the derivatives
1
were furnished by H NMR, IR and EI-MS spectral analysis. All the synthesized compounds were screened for α-chemotrypsin and
antibacterial activities.
Keywords: Substituted anilines, 4-Chlorobenzenesulfonyl chloride, Enzyme inhibition study.
1
0-12
of our prior research work on chlorinated sulfonamide , the
further synthesis was brought about to prepare new competent
that might work as a remedy of several diseases owing to their
splendid therapeutic potential.
INTRODUCTION
Sulfonamides bear sulfamoyl (-SO
2
NH-) group and are
pharmacologically significant class of compounds. Sulfamoyl
group is considered crucial for drugs being used extensively
as anticancer, antimicrobial, antiviral, antihydrod, antiinfla-
mmatory and antitumor agents along with carbonic anhydrase
EXPERIMENTAL
1
inhibitors . Because of less toxicity, increased activity and less
All the chemical reagents were purchased through local
suppliers, Merck andAlfaAeser branded and did not processed
for further purification. All solvents used were of analytical
grade. Thin layer chromatography (TLC) was applied to confirm
the purity of the synthesized compounds with solvent systems
consisting of different percentages of ethyl acetate and n-
hexane. Developed TLC plates were visualized by UV lamp
at wavelength of 254 nm and UV inactive reagents were identi-
fied by spraying with ceric sulfate solution. Infrared spectra
were recorded on a Jasco-320-A spectrophotometer by KBr
pellet method. Melting points were recorded by the help of
Griffin-George melting point apparatus using open capillary
2
-6
cost, sulfonamides are widely used as antibacterial agents .
The p-aminobenzoic acid (PABA) is involved in synthesis of
folic acid in bacterial cell. Sulfonamides are related to p-amino-
benzoic acid in structure and so inhibit p-aminobenzoic acid
conversion to folic acid. Finally the synthesis of purine and
1
DNA is inhibited . Sulfonamide synthesis generally takes place
by nucleophilic substitution reactions.Amine, the nucleophile,
7
attacks on sulfonyl chloride while electrophilic substitution
reaction takes place during N-substitution of these resulted
molecules. Sulfonamides have been reported in more than 30
8
drugs of vast clinical applications . These molecules also find
9
their applications in animal husbandry and food additives .
1
tube and uncorrected. H NMR spectra were recorded in
Literature survey revealed that small variations in the struc-
ture of sulfonamides can cause significant changes in biological
activity. These results insisted scientists to focus on synthesis
of variety of N-substituted derivatives of sulfonamides to
introduce new drug candidates with enhanced biological poten-
tial. The demonstrated research work was a successful attempt
to synthesize pharmacologically potent compounds. In sequence
3
CD OD on a Bruker spectrometers operating at 500 MHz. The
chemical shift values are given in ppm scale while TMS was
used as reference and the coupling constants (J) are mentioned
in Hz. Mass spectra (EI-MS) were taken on a JMS-HX-110
spectrometer.
General procedure for synthesis of different chlorinated
sulfonamides (3a-b): Alkoxy (un)substituted anilines (0.001

α-Chymotrypsin assay: α-Chymotrypsin inhibition
1
(C-N), 557 (C-Cl); H NMR (500 MHz, CD OD, ppm): δ 7.69
3
7
2 Aziz-ur-Rehman et al.
Asian J. Chem.
mol; 2a-b) were dispersed in 100 mL round bottom flask
containing 50 mL distilled water. 10 % aqueous Na CO solu-
1H, H-4), 6.88 (dt, J = 9, 1.5 Hz, 1H, H-5), 6.81 (d, J = 8.5
Hz, 1H, H-3), 3.61 (q, J = 7.5 Hz, 2H, H-1"), 3.50 (s, 3H,
2
3
tion was used to maintain the pH = 9-10. 4-Chlorobenzene-
sulfonyl chloride (0.001 mol; 1) was introduced to reaction
flask gradually in 10-15 min sustaining the pH at 9-10. Reac-
tion contents were allowed to stir for 3-5 h at room temperature.
The reaction coordinates were checked by TLC (n-hexane:
ethyl acetate; 70:30) time by time till completion. Reaction
mixture was acidified by adding 3-4 mL concentrated HCl
slowly to bring the pH to 2-3. The solid precipitates were
filtered and washed with distilled water to obtain the products
CH
3
O-2), 1.04 (t, J = 7.5 Hz, 2H, H-2"); EIMS (m/z): 327 [M
+
] , 150 [M-
•
+
•+
+ 2] , 325 [M] , 261 [M-SO
•+
] , 175 [C
2
6
H
4
ClSO
2
+
] , 122 [M-C
+
] , 111 [C
+
Cl] , 107 [M-
C
6
H
4
ClSO
2
8
H
8
ClSO
2
H
6 4
•+
•+
C
8
H
9
ClNSO
2
6 4
] , 76 [C H ] .
N-Phenyl-N-benzyl-4-chlorobenzenesulfonamide (8a):
White amorphous solid; Yield: 83 %; m.p. 112-114 °C; m.f.:
-1
19 2
C H16NSO Cl; m.w.: 357; IR (KBr, νmax, cm ): 3053 (Ar-H),
1
1532 (Ar C=C), 1416 (-SO
2
-), 1144 (C-N), 557 (C-Cl); H
NMR (500 MHz, CD OD, ppm): δ 7.68 (d, J = 9 Hz, 2H,
3
3
a-b on drying. Precipitates were recrystallized by methanol.
Procedure for the synthesis of N-[alkoxy (un)substituted
H-2', H-6'), 7.47 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.23 (d, J = 10
Hz, 2H, H-2, H-6), 7.18-7.14 (m, 5H, H-2" to H-6"), 7.10-
7.05 (m, 3H, H-3 to H-5), 4.71 (s, 2H, H-7"); EIMS (m/z):
phenyl]-N-alkyl/aralkyl-4-chlorobenzenesulfonamide (7a-
b, 8a-b, 9a-b): Compounds, 3a-b (0.01 mol) were dissolved
in 10 mL polar aprotic solvent DMF in a 100 mL round bottom
flask. Sodium hydride (0.01 mol) was introduced to reaction
contents to activate the reaction and set to stir for 0.5 h at room
temperature. The electrophiles ethyl iodide, benzyl chloride
and 4-chlorobenzyl chloride (4-6; 0.01 mol) were added to
reaction contents and stirred for 4-5 h to yield the target com-
pounds, 7a-b, 8a-b and 9a-b. On completion ice cold distilled
water was added to the reaction mixture along with vigorous
shaking to yield the precipitates. The precipitates formed were
left for 10-15 min undisturbed and then filtered, washed with
water and dried to yield the target compounds, 7a-b, 8a-b and
•+
•+
•+
+
359 [M + 2] , 357 [M] , 293 [M-SO ] , 175 [C
2
6
H
4
ClSO ] ,
2
+
] , 111 [C
+
Cl] , 92 [M-C1
+
] ,
182 [M-C
6
H
4
ClSO
2
H
6 4
3
H10ClSO
2
•
+
6 4
76 [C H ] .
N-(2-Methoxyphenyl)-N-benzyl-4-chlorobenzenesul-
fonamide (8b): Light pink amorphous solid;Yield: 87 %; m.p.
110-112 °C; m.f.: C20
H
18NSO
3
Cl; m.w.: 387; IR (KBr, νmax
cm ): 3057 (Ar-H), 1535 (Ar C=C), 1413 (-SO -), 1143
OD, ppm): δ 7.66
,
-
1
2
1
(C-N), 565 (C-Cl); H NMR (500 MHz, CD
3
(d, J = 9 Hz, 2H, H-2', H-6'), 7.45 (d, J = 8.5 Hz, 2H, H-3', H-
5'), 7.41 (d, J = 8.5, 2.5 Hz, 1H, H-6), 7.18-7.12 (m, 5H, H-2"
to H-6"), 7.12 (dt, J = 8.5, 2 Hz, 1H, H-4), 6.87 (dt, J = 9.5,
2.5 Hz, 1H, H-5), 6.81 (d, J = 9.5 Hz, 1H, H-3), 4.68 (s, 2H,
•+
9a-b.
H-7"), 3.50 (s, 3H, CH O-2); EIMS (m/z): 389 [M + 2] , 387
3
•
+
•+
] , 175 [C
+
] , 212 [M-C
+
] ,
Antibacterial activity: The antibacterial activity method
[M] , 323 [M-SO
2
6
H
4
ClSO
2
6
H
4
ClSO
2
+
] , 111 [C
+
was based on the principle that microbial cell number or
microbial growth was directly related to the log phase of growth
122 [M-C13
H
10ClSO
2
6
H
4
Cl] , 107 [M-
•
+
•+
C
13
H
11ClNSO
2
] , 76 [C
N-Phenyl-N-[(4-chlorophenyl)methyl]-4-chlorobenzene-
sulfonamide (9a): White amorphous solid;Yield: 82 %; m.p.
118-120 °C; m.f.: C19 Cl ; m.w.: 392; IR (KBr, νmax
cm ): 3055 (Ar-H), 1534 (Ar C=C), 1414 (-SO -), 1143
6 4
H ] .
1
0,13
with increase in absorbance of broth medium
Lipoxygenase assay: Lipoxygenase activity was assayed
.
1
4,15
according to the reported method
cations.
but with slight modifi-
H15NSO
2
2
,
-
1
2
1
6,17
assay was carried out according to the reported method
.
(d, J = 9 Hz, 2H, H-2', H-6'), 7.47 (d, J = 8.5 Hz, 2H, H-2", H-
6"), 7.45 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.22 (d, J = 10 Hz,
2H, H-2, H-6), 7.31 (d, J = 8.5 Hz, 2H, H-3", H-5"), 7.08-
7.04 (m, 3H, H-3 to H-5), 4.61 (d, J = 13.5 Hz, 1H, Ha-7"),
Statistical analysis: All the measurements were done in
triplicate and statistical analysis was performed by Microsoft
Excel 2010. Results are presented as mean ± sem.
•
+
4
.17 (d, J = 13.5 Hz, 1H, Hb-7"); EIMS (m/z): 394 [M + 2] ,
•+
] , 175 [C
Spectral characterization of all the synthesized derivatives
•
92 [M] , 328 [M-SO
+
+
] , 217 [M-
3
2
6
H
4
ClSO
2
N-Phenyl-N-ethyl-4-chlorobenzenesulfonamide (7a):
White amorphous solid; Yield: 79 %; m.p. 116-118 °C; m.f.:
+
] , 92 [M-C13
+
] , 111 [C
+
Cl] , 76
C
6
H
4
ClSO
2
H
9
Cl
2
SO
2
6
H
4
•+
[C
6
H
4
] .
N-(2-Methoxyphenyl)-N-[(4-chlorophenyl)methyl]-4-
chlorobenzenesulfonamide (9b): White amorphous solid;
Yield: 83 %; m.p. 112-114 °C; m.f.: C20 Cl ; m.w.:
22; IR (KBr, νmax, cm ): 3055 (Ar-H), 1531 (Ar C=C), 1411
-1
14 2
C H14NSO Cl; m.w.: 295; IR (KBr, νmax, cm ): 3056 (Ar-H),
1
1
537 (Ar C=C), 1421 (-SO
NMR (500 MHz, CD OD, ppm): δ 7.68 (d, J = 9 Hz, 2H, H-
', H-6'), 7.45 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.21 (d, J = 10
Hz, 2H, H-2, H-6), 7.09-7.04 (m, 3H, H-3 to H-5), 3.56 (q, J
2
-), 1151 (C-N), 561 (C-Cl); H
3
H17NSO
3
2
2
-1
4
1
(
-SO
ppm): δ 7.65 (d, J = 9 Hz, 2H, H-2', H-6'), 7.48 (d, J = 8.5 Hz,
H, H-2", H-6"), 7.44 (d, J = 8.5 Hz, 2H, H-3', H-5'), 7.40
dd, J = 13.5, 2.5 Hz, 1H, H-6), 7.27 (d, J = 8.5 Hz, 2H, H-3",
H-5"), 7.11 (ddd, J = 13.5, 3 Hz, 1H, H-4), 6.88 (ddd, J =
2 3
-), 1141 (C-N), 561 (C-Cl); H NMR (500 MHz, CD OD,
=
7.5 Hz, 2H, H-1"), 1.03 (t, J = 7.5 Hz, 2H, H-2"); EIMS
•+
] , 175
•
m/z): 297 [M + 2] , 295 [M] , 231 [M-SO
+
•+
(
[
[
2
2
+
+
+
C
6
H
4
ClSO
2
] , 120 [M-C
Cl] , 77 [M-C ClNSO
N-(2-Methoxyphenyl)-N-ethyl-4-chlorobenzenesul-
fonamide (7b): White amorphous solid; Yield: 78 %; m.p.
06-108 °C; m.f.: C15 Cl; m.w.: 325; IR (KBr, νmax
cm ): 3062 (Ar-H), 1532 (Ar C=C), 1422 (-SO -), 1153
OD, ppm): δ 7.65
d, J = 9 Hz, 2H, H-2', H-6'), 7.44 (d, J = 8.5 Hz, 2H, H-3',
6
H
4
ClSO
2
] , 92 [M-C
8
H
8
ClSO
2
] , 111
(
+
•+
•+
C
6
H
4
H
8 9
2 6 4
] , 76 [C H ] .
1
4
0.5, 2.5 Hz, 1H, H-5), 6.81 (dd, J = 13.5, 1.5 Hz, 1H, H-3),
.63 (d, J = 13.5 Hz, 1H, Ha-7"), 4.13 (d, J = 13.5 Hz, 1H,
1
H16NSO
3
,
•+
O-2); EIMS (m/z): 424 [M + 2] ,
Hb-7"), 3.50 (s, 3H, CH
•+
22 [M] , 358 [M-SO
3
-
1
2
•+
] , 175 [C
+
] , 247 [M-
4
2
6
H
4
ClSO
2
1
(C-N), 563 (C-Cl); H NMR (500 MHz, CD
3
+
] , 122 [M-C1
+
] , 111 [C
+
Cl] , 107 [M-
C
6
H
4
ClSO
2
3
H Cl SO
9 2
2
H
6 4
(
•+
2 6 4
•+
NSO ] , 76 [C H ] .
C
13
H
10Cl
2
H-5'), 7.40 (d, J = 8 Hz, 1H, H-6), 7.11 (dt, J = 8.5, 1.5 Hz,

Vol. 27, No. 1 (2015)
Synthesis of N-(Un)Substituted-N-(2-Methoxyphenyl/Phenyl)-4-Chlorobenzenesulfonamides 73
appeared at m/z 392. Other characteristic peaks appeared at
m/z 328, 217 and 175 after the loss of SO , loss of phenyl-
RESULTS AND DISCUSSION
2
A series of chlorinated sulfonamides have been synthe-
sized as outlined in Scheme-I. All derivatives were subjected
for antibacterial activity against four Gram-negative
sulfonyl group and due to chlorinated phenylsulfonyl cation
respectively. IR spectrum revealed characteristics peaks at 1414
for sulfonyl stretching, 1534 for carbon to carbon double bond
(
K. pneumonae, E. coli, P. aeroginosa and S. typhi) and two
1
stretching and 3055 for aromatic proton stretching. In the H
Gram-positive (B. subtilis and S. aureus) bacteria. The aim to
synthesize these compounds was to introduce new potent drug
candidates that might find applications in the drug develop-
ment.
NMR spectrum the p-chlorophenyl sulfonyl group revealed
signals at δ 7.69 and 7.45 each as doublet with integration of
two protons each and coupling constant of 9 & 8.5 Hz,
respectively. Signals of N-phenyl group resonated at δ 7.22
The parent sulfonamides, N-alkoxy (un)substituted 4-
chlorobenzenesulfonamide (3a-b) were yielded by coupling
of alkoxy (un)substituted aniline (2a-b) with 4-chlorobenzene-
sulfonyl chloride (1) in the presence of sodium carbonate
solution at pH 9-10. The products were produced after addition
of dilute hydrochloric acid drop by drop. Excess use of acid
was avoided to retain the yield. Compound (3a-b) on reaction
with different alkyl halides such as ethyl iodide (4), benzyl
chloride (5) and 4-chlorobenzyl chloride (6) yielded the N-
substituted derivatives of sulfonamides, 7a-b, 8a-b and 9a-b,
respectively. Sodium hydride was used to provide basic medium
in DMF as solvent. All the products were obtained by treating
with cold distilled water. Spectral data affirmed the structures
of all the derivatives. Compound 9a was produced as white
amorphous solid in 82 % yield having melting point 118-
(
d, J = 10 Hz, 2H, H-2, H-6) and 7.08-7.04 (m, 3H, H-3 to H-
), while N-(4-chlorophenyl)methyl group showed signals at
5
δ 7.47 and as multiplet integrated for five protons indicated
the presence of benzyl group, the methylene of benzyl group
revealed at d 4.84. Signals appeared at δ 1.69-1.53 (m, 4H, H-
2
, H-6) and 7.31 each as doublet having integration of two
protons and J value of 8.5 Hz. All these spectral data affirmed
the structure of 9a as N-phenyl-N-[(4-chlorophenyl) methyl]-
4
-chlorobenzenesulfonamide. Similarly the structures of all
other compounds were elaborated by the help of these
spectroscopic techniques.
Antibacterial and enzyme inhibition activity: All the
compounds were screened for antibacterial activity and enzyme
inhibition potential and results are depicted in Tables 1 to 3. It
was observed that most of the compounds were active as anti-
bacterial agents while enzyme inhibition potential was not
appreciable.
120 °C with molecular formula C19
2 2
H15NSO Cl and molar mass
392. The structure and mass were established by different
spectroscopic techniques. In EI-MS molecular ion peak
O
O
O
O
S
N
H
S
H N
2
Aq. Na
CO
2 3
Cl
R
stirring, pH= 9-10
Cl
Cl
R
3a-b
NaH, DMF
stirring at rt
2
a-b
1
C H CH Cl
6
4-ClC H CH Cl
6 4 2
5
2
C H I
2
5
4
5
6
O
O
O
O
O
N
O
S
S
S
N
N
R
R
R
CH2
a-b
H C
2
H C
2
Cl
Cl
Cl
H C
3
7
8a-b
9a-b
Cl
Compd.
7
R
a,8a,9a
b,8b,9b
Scheme-I: Synthesis of N-((alkoxy (un)substituted)phenyl)-4-chloro-benzenesulfonamide
H
7
2-OCH
3

7
4 Aziz-ur-Rehman et al.
Asian J. Chem.
TABLE-1
PERCENTAGE INHIBITION VALUES OF ANTIBACTERIAL ACTIVITY OF SYNTHESIZED DERIVATIVES
Percentage inhibition
Compound
S. typhi (-)
48.46 ± 1.46
73.66 ± 0.46
-
E. coli (-)
78.88 ± 2.79
73.67 ± 0.11
-
K. pneumonae (-)
51.09 ± 1.74
64.85 ± 0.15
-
B. subtilis (+)
69.15 ± 1.95
72.22 ± 2.05
-
S. aureus (+)
66.65 ± 2.12
82.08 ± 2.51
-
P. aeroginosa (-)
73.67 ± 1.42
78.64 ± 0.82
-
7
a
7b
8a
8
b
52.68 ± 0.65
47.67 ± 3.12
37.61 ± 2.86
91.21 ± 0.22
43.17 ± 2.13
53.74 ± 2.34
20.42 ± 1.90
92.00 ± 0.23
50.31 ± 0.61
42.51 ± 1.61
37.10 ± 2.31
90.63 ± 0.12
56.43 ± 4.52
54.59 ± 1.19
34.22 ± 1.35
90.35 ± 0.21
55.19 ± 4.42
66.22 ± 2.57
37.04 ± 2.80
91.98 ± 0.04
66.23 ± 1.4
47.68 ± 2.50
47.82 ± 4.82
91.38 ± 0.01
9
a
9b
Ciprofloxacin
TABLE-2
MIC VALUES OF ANTIBACTERIAL ACTIVITY OF SYNTHESIZED DERIVATIVES
MIC values
Compound
S. typhi (-)
E. coli (-)
K. pneumonae (-)
P. aeroginosa (-)
B. subtilis (+)
13.51 ± 1.99
12.63 ± 1.48
-
S. aureus (+)
12.01 ± 2.34
12.28 ± 1.44
-
7a
7b
8a
8b
9a
9b
-
10.33 ± 2.98
19.45 ± 1.95
10.45 ± 0.63
12.55 ± 1.00
11.78 ± 1.34
13.26 ± 0.89
9.8 ± 0.65
-
-
-
-
18.34 ± 1.60
-
19.82 ± 0.32
13.66 ± 1.11
16.05 ± 1.21
17.89 ± 1.41
-
13.66 ± 1.99
13.27 ± 1.77
-
-
17.88 ± 1.34
-
-
-
-
-
-
Ciprofloxacin
9.27 ± 1.58
8.06 ± 1.07
8.51 ± 0.14
8.48 ± 1.91
9.04 ± 1.86
8.95 ± 1.33
TABLE-3
α-CHEMOTRYPSIN ENZYME INHIBITION
ACTIVITY OF SYNTHESIZED DERIVATIVES
vivo activity by the pharmacological industries to evaluate their
toxicity and hence as new drug candidate.
Concentration
Chemotrypsin
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8a
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9a
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0.5
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52.56 ± 0.06
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.
G.E. Cami, R.D. Arellano, M.C. Del, S. Fustero and J.C. Pedregosa, J.
Argentine Chem. Soc., 94, 5 (2006).
respectively relative to that of standard, 8.06 ± 1.07 and 8.48
±
1.91, respectively. Compound 7b was active against all the
bacterial strains (S. typhi, E.coli, K. pneumonae, P. aeroginosa,
B. subtilis and S. aureus) with MIC values of 12.55 ± 1, 11.78
.
I. Argyropoulou, A. Geronikaki, P. Vicini and F. Zani, ARKIVOC, 89
(2008).
0. H. Khalid, Aziz-ur-Rehman, M.A. Abbasi, A. Malik, S. Rasool, K.
Nafeesa, I. Ahmad and S. Afzal, J. Saudi Chem. Soc., doi:10.1016/
j.jscs.2013.05.001.
±
1.34, 13.26 ± 0.89, 9.8 ± 0.65 12.63 ± 1.48 and 12.28 ±
.44, respectively, as compared to ciprofloxacin with MIC
values of 9.27 ± 1.58, 8.06 ± 1.07, 8.51 ± 0.14, 8.48 ± 1.91,
.04 ± 1.86 and 8.95 ± 1.33, respectively. All these results
1
1
1
1
1. H. Khalid,Aziz-ur-Rehman, M.A.Abbasi and K.M. Khan, Int. J. Pharm.
Pharm. Sci., 4, 443 (2012).
2. Aziz-ur-Rehman, S. Rasool, M.A. Abbasi, K.M. Khan, M. Asraf and I.
Afzal, Asian J. Pharm. Bio. Res., 2, 100 (2012).
3. N.M. Tariq, S.U. Wisam, H.M. Faik and T.H. Mayson, Pak. J. Chem.,
9
showed that 7b was most active against P. aeroginosa. The
results of enzyme inhibition analysis of these compounds were
not too much significant against α-chemotrypsin enzyme.
3, 1 (2013).
14. Aziz-ur-Rehman, A. Fatima, M.A. Abbasi, S. Rasool, A. Malik, M.
Ashraf, I. Ahmad and S.A. Ejaz, J. Saudi Chem. Soc., doi:10.1016/j.
jscs.2013.02.006.
Conclusion
1
5. Aziz-ur-Rehman, S. Tahir, M.A. Abbasi, S. Rasool, A. Siddiqa, Awais-
ur-Rehman, A. Muhammad and A. Sharif, Asian J. Chem., 25, 9000
The molecules were synthesized in awesome amounts and
1
their structures were corroborated through H NMR with
(
2013).
6. M.R.H. Siddiqui, J. Chem., Article ID 780939 (2013).
sufficient support of IR and EIMS spectral data. It was noted
that the most of the derivatives were moderately good anti-
bacterial agents with no activity against α-chymotrypsin
enzyme. Furthermore, these molecules can be analyzed for in
1
17. M.A. Abbasi, M.A. Lodhi, V.U. Ahmad and M.I. Choudhary, J. Asian
Nat. Prod. Res., 11, 933 (2009).