Synthesis and biological evaluation of some novel 4-phenyldiazenyl-4'-[(4- chlorobenzyl)oxy]biphenyl derivatives as antibacterial agents

Article abstract of DOI:10.4067/S0717-97072014000100007

A series of five new 4-phenyldiazenyl-4'-[(4-chlorobenzyl)oxy]biphenyls have been synthesized by condensing different sodium salts of some 4'-phenyldiazenylbiphenyl- 4-ols with 1-chloro-4-(chloromethyl)benzene. These compounds have been characterized by elemental analysis (C, H, N) and electronic, IR, 1H NMR and mass spectrometry studies. The obtained compounds were assayed for their antibacterial activity against some bacteria by disk diffusion method.

Full text of DOI:10.4067/S0717-97072014000100007

J. Chil. Chem. Soc., 59, Nº 1 (2014)
SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NOVEL 4-PHENYLDIAZENYL-4’-[(4-
CHLOROBENZYL)OXY]BIPHENYL DERIVATIVES AS ANTIBACTERIAL AGENTS
ANCA MOANTA
University of Craiova, Faculty of Exact Sciences, Department of Chemistry, 107i Calea Bucuresti Street, 200512, Craiova, Romania
(Received: January 17, 2013 - Accepted: August 19, 2013)
ABSTRACT
Aseriesoffivenew4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenylshavebeensynthesizedbycondensingdifferentsodiumsaltsofsome4’-phenyldiazenyl-
biphenyl-4-ols with 1-chloro-4-(chloromethyl)benzene. These compounds have been characterized by elemental analysis (C, H, N) and electronic, IR, 1H NMR
and mass spectrometry studies. The obtained compounds were assayed for their antibacterial activity against some bacteria by disk diffusion method.
Keywords: antibacterial activity, azomonoether, FTIR spectra, UV-Vis spectra, mass spectra, NMR spectra.
solution, the reaction temperature was kept below 5 °C in order to stabilize
diazonium ions. This solution was slowly added at 0 – 5 °C to 4-biphenylol
(6.1 g, 36 mmol) in 10% NaOH solution and the pH was adjusted to 8 – 9
with concentrated NaOH solution. The obtained solution was stirred at room
temperature for 6 h. The precipitate was collected by filtration, washed three
times with distilled water, recrystallized in a mixture of 50 mL of ethanol and
100 mL of water and vacuum dried. Compounds 2a-e were obtained as orange
crystalline solids.
INTRODUCTION
Many synthetic compounds with antimicrobial activity have been
discovered and are of considerable importance from the standpoint of research
and practical applications: aminoglycosides1, cephalosporins2, lipopeptides3,
sulfonamides4-7, macrolides8, oxazolidinones9, quinolones10, and pyrimidines
derivatives11.
The development of new antimicrobial drugs is a very important objective
not only from the rapidly developing drug resistance point of view, but also
regarding the unsatisfactory status of present treatments of bacterial and fungal
infections and drug side-effects. In recent years there has been a great deal of
interest in exploiting multiple proximal functional groups in the design of novel
structures capable of performing a variety of functions. Synthesis of molecules
that are novel but still resemble known biologically active molecules by virtue
of the presence of some critical structural features is an essential component of
the search for new leads in drug design.
Synthesis of 4’-phenyldiazenylbiphenyl-4-ol (2a)
Compound (2a) was obtained using the general procedure I with 3.35 g
of aniline (36 mmol). Yield 84.3%; m.p.112 °C; Anal. Calcd. for C18H14N2O
(%): C 78.83, H 5.10, N 10.21; Found (%): C 78.69, H 4.97, N 10.15; IR
1
(powder; cm-1): 1610 (N=N), 1424 (N=N), 3033 (CAr-OH), 1155 (Ar-N); H
NMR (60 MHz, CCl , δ / ppm): 6.4 (m, 13H, aromatic), 5.3 (s, 1H, OH); UV-
Vis (dioxane) (λ / 4nm (εmax / L mol-1 cm-1)): 226 (10517), 265 (19105), 327
(16607), 424 (45m4a7x ).
Synthesis of 4’-(4-methyl-phenyldiazenyl)biphenyl-4-ol (2b)
During the last few decades, considerable attention has been devoted to
synthesis of azoderivatives possessing such different types of bioactivities
like: antibacterial12,13, antifungal14, anti-inflammatory15,16, antiviral17 and anti-
HIV activities18. In recent years, biphenyl derivatives are an extensively
investigated class of compounds, which exhibits various biological activities,
Compound (2b) was synthesized using the above procedure with 3.85 g
of p-toluidine as aromatic amine. Yield 82.8%; m.p. 115 °C; Anal. Calcd for
C19H16N2O (%): C 79.16, H 5.55, N 9.72; Found (%): C 79.01, H 5.63, N 9.64;
IR (powder; cm-1): 1608 (N=N), 1455 (N=N), 3019 (C -OH), 1165 (Ar-N); 1H
NMR (60 MHz, CCl4, δ / ppm: 6.6 (m, 12H, aromatic)A,r5.3 (s, 1H, OH), 2.4 (s,
3H, CH ); UV-Vis (dioxane) (λ / nm (εmax / L mol-1 cm-1)): 227 (13790), 264
(24002)3, 335 (21577), 409 (829m7a)x.
such as anti-tuberculosis19, antibacterial20, antifungal20 and anticancer21,22
.
These observations place new emphasis on the synthesis of azoderivatives with
a view to incorporation of a biphenyl fragment, for the evaluation of associated
antibacterial activity.
Synthesis of 4’-(4-chloro-phenyldiazenyl)biphenyl-4-ol (2c)
Compound (2c) was synthesized using the above procedure with 4.6 g of
p-chloroaniline as aromatic amine. Yield: 78.7%; m.p. 126 °C; Anal. Calcd.
for C18H13ClN2O (%): C 70.01, H 4.21, N 9.07; Found (%): C 69.83, H 4.15, N
9.15; IR (powder; cm-1): 1580 (N=N), 1447 (N=N), 3029 (CAr-OH), 1165 (Ar-
N), 593 (Ar-Cl); 1H NMR (60 MHz, CCl4, δ / ppm): 6.8 (m, 12H, aromatic),
5.4 (s, 1H, OH); UV-Vis (dioxane) (λ / nm (εmax / L mol-1 cm-1)): 228 (12272),
264 (24395), 335 (22690), 421 (6955m).ax
As part of our continuous research in the synthesis of biologically active
azocompounds23-25
,
five new 4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]
biphenyls have been synthesized and their structures and antibacterial activities
are reported in this paper.
EXPERIMENTAL
Synthesis of 4’-(2-chloro-phenyldiazenyl)biphenyl-4-ol (2d)
Materials
Compound (2d) was synthesized using the above procedure with 4.6 g of
o-chloroaniline as aromatic amine. Yield: 84.2%; m.p. 111 °C; Anal. Calcd.
for C18H13ClN2O (%): C 70.01, H 4.21, N 9.07; Found (%): C 69.96, H 4.17, N
8.88; IR (powder; cm-1): 1593 (N=N), 1451 (N=N), 3026 (CAr-OH), 1161 (Ar-
N), 696 (Ar-Cl); 1H NMR (60 MHz, CCl4, δ / ppm): 7.2 (m, 12H, aromatic), 5.6
(s, 1H, OH) UV-Vis (dioxane) (λmax / nm (εmax / L mol-1 cm-1)): 221 (4717), 262
(13722), 334 (10657), 433 (3287);.
Aniline, p-toluidine, o-chloroaniline, p-chloroaniline, 3,4-dichloroaniline,
4-biphenylol and 1-chloro-4-(chloromethyl)benzene were purchased from
Merck and were used without purification.
Methods
The melting point was determined using a Sanyo Gallenkamp melting point
apparatus without correction. The analyses of carbon, hydrogen and nitrogen
were performed with a Carlo Erba 1108 analyzer. The UV-Vis measurements
were carried out with a UV-Vis Varian Cary-50 Bio spectrophotometer.
FT-IR spectra of these compounds were recorded on a Bruker ATR ZnSe
spectrophotometer, within the range of 4000 - 550 cm-1, at room temperature
Synthesis of 4’-(3,4-dichloro-phenyldiazenyl)biphenyl-4-ol (2e)
Compound (2e) was synthesized using the above procedure with 5.83 g
of 3,4-dichloroaniline as aroamtic amine. Yield: 91.5%; m.p. 147 °C; Anal.
Calcd. for C18H12Cl2N2O (%): C 62.97, H 3.50, N 8.16; Found (%): C 62.83,
H 3.42, N 8.03; IR (powder; cm-1): 1574 (N=N), 1451 (N=N), 3030 (CAr-OH),
1
with a spectral resolution of 2 cm-1. The H NMR spectra were registered on
Varian EM-360, 60 MHz spectrometer, using CCl as solvent and TMS as
internal standard. Mass spectra were run with HPGC4-MS 5890 spectrometer at
70 eV and at 250°C (the source temperature).
1
1161 (Ar-N), 692 (Ar-Cl); H NMR (60 MHz, CCl4, δ / ppm): 7.2 (m, 11H,
aromatic), 5.67 (s, 1H, OH); UV-Vis (dioxane) (λ / nm (εmax / L mol-1 cm-1)):
228 (31975), 260 (9167), 338 (7340), 432 (2017).max
General procedure I for the synthesis of 2a-e26
General procedure II for the synthesis of 3a-e
A solution of sodium nitrite (36 mmol) in 75 mL of water was slowly
added under stirring to a solution of amine (36 mmol) dissolved in 150 mL of
2 mol L-1 HCl solution, cooled at 0 – 5 °C26. During the addition of the NaNO2
In a 100 cm3 three necked flask equipped with a condenser, stirrer and
thermometer, 6.67 mmoles of azophenol and 0.266 g (6.67 mmoles) of sodium
e-mail: moantaanca@yahoo.com
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J. Chil. Chem. Soc., 59, Nº 1 (2014)
Determination of relative percentage of inhibition
hydroxide were added in 20 mL of benzene and 20 mL of ethanol. The reaction
mixture was stirred at room temperature for 90 minutes then the resulted water
was isolated as a water-benzene-ethanol azeotropic mixture. To anhydrous
azophenoxide, 1.07 g (6.67 mmoles) of 1-chloro-4-(chloromethyl)benzene
were added. The mixture was refluxed for five hours. After cooling at room
temperature, compounds 3a-e were formed as yellow-orange precipitates. The
precipitates were filtered, washed with water and ethanol and dried at 105
°C in a heating chamber. After repeated recrystallizations from toluene, pure
compounds were obtained as yellow-orange crystals.
The relative percentage of inhibition of the tested compounds with
respect to standard drug was calculated by using the following formula28:
(1)
Where,
I%: Relative percentage inhibition
Synthesis of 4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenyls (3a)
Compound (3a) was obtained using the general procedure II with 1.82 g
of 4’-phenyldiazenylbiphenyl-4-ol. Yield: 85.4%; m.p. 182 °C; Anal. Calcd.
for C25H19ClN2O (%): C 75.28, H 4.80, N 7.02; Found (%): C 75.12, H 4.76,
N 6.93; IR (powder; cm-1): 1604 (N=N), 1411 (N=N), 1264 (C-O-Casym), 1014
x: total area of inhibition of the tested compound
y: total area of inhibition of the solvent
z: total area of inhibition of the standard drug
The total area of the inhibition was calculated by using area = πr2;
where, r = radius of zone of inhibition.
1
(C-O-Csym), 748 (C-Cl); H NMR (60 MHz, CCl4, δ / ppm): 7.3 (m, 17H,
aromatic); 5.1 (s, 2H, CH2); MS (m/z, (relative abundance, %)): 398 (M+, 6.5),
125 (100); UV-Vis (dioxane) (λmax / nm (εmax / L mol-1 cm-1)): 234 (27400), 260
(28600), 338 (10800), 432 (4600);.
RESULTS AND DISCUSSION
The new azomonoethers were prepared using the etherification of the
corresponding sodium salts of substituted 4’-phenyldiazenyl-biphenyl-4-
ols with 1-chloro-4-(chloromethyl)benzene in alkaline medium (Scheme
1) employing Williamson method23-25. The sodium salts were obtained from
the corresponding 4’-phenyldiazenyl-biphenyl-4-ols dissolved in an ethanol-
benzene mixture (1 : 1, in volumes) and sodium hydroxide. These salts are
obtained in anhydrous state by azeotropic distillation of the benzene-ethanol-
water mixture.
Synthesis
of
4-(4-methyl-phenyldiazenyl)-4’-[(4-chlorobenzyl)oxy]
biphenyl (3b)
Compound (3b) was synthesized using the above procedure with 1.92 g of
4’-(4-methyl-phenyldiazenyl)biphenyl-4-ol as azophenol. Yield: 81.6%; m.p.
174 °C; Anal. Calcd. for C26H21ClN2O (%): C 75.63, H 5.13, N 6.78; Found
(%): C 75.57, H 5.09, N 6.73; IR (powder; cm-1): 1601 (N=N), 1411 (N=N),
1
1265 (C-O-Casym), 1013 (C-O-C ), 743 (C-Cl); H NMR (60 MHz, CCl4, δ
/ ppm): 7.2 (m, 16H, aromatic);s5ym.0 (s, 2H, CH2); 2.2 (s, 3H, CH3); MS (m/z,
(relative abundance, %)): 412 (M+, 12), 125 (100); UV-Vis (dioxane) (λmax / nm
(ε / L mol-1 cm-1)): 236 (17800), 262 (20400), 339 (9200), 448 (4000).
maxSynthesis
of
4-(4-chloro-phenyldiazenyl)-4’-[(4-chlorobenzyl)oxy]
biphenyl (3c)
Compound (3c) was synthesized using the above procedure with 2.05 g
4-(4-chloro-phenyldiazenyl)biphenyl-4-ol as azophenol. Yield: 81.4%; m.p.
153 °C; Anal. Calcd. for C25H18Cl2N2O (%): C 69.29, H 4.19, N 6.46; Found
(%): C 69.18, H 4.15, N 6.34; IR (powder; cm-1): 1560 (N=N), 1400 (N=N),
1
1265 (C-O-Casym), 1013 (C-O-Csym), 747 (C-Cl); H NMR (60 MHz, CCl4, δ /
ppm): 7.4 (m, 16H, aromatic), 5.2 (s, 2H, CH2); MS (m/z, (relative abundance,
%)): 432 (M+, 4), 125 (100); UV-Vis (dioxane) (λmax / nm (εmax / L mol-1 cm-1)):
235 (21600), 263 (22600), 344 (9400), 440 (4200).
Synthesis
of
4-(2-chloro-phenyldiazenyl)-4’-[(4-chlorobenzyl)oxy]
biphenyl (3d)
Compound (3d) was synthesized using the above procedure with 2.05 g
4-(2-chloro-phenyldiazenyl)biphenyl-4-ol as azophenol. Yield: 88.3%; m.p.
161 °C; Anal. Calcd. for C25H18Cl2N2O (%): C 69.29, H 4.19, N 6.46; Found
(%): C 69.21, H 4.17, N 6.38; IR (powder; cm-1): 1604 (N=N), 1413 (N=N),
Scheme 1: Synthesis of 4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]
biphenyls 3a-e
The composition and purity of synthesized azoethers was confirmed by
elemental analyses (see experimental sections). These obtained compounds
were crystalline yellow-orange powders. They are stable at room temperature
and all compounds are insoluble in water.
1
1264 (C-O-Casym), 1014 (C-O-Csym), 746 (C-Cl); H NMR (60 MHz, CCl4, δ /
ppm): 7.7 (m, 16H, aromatic); 5.4 (s, 2H, CH2); MS (m/z, (relative abundance,
%)): 432 (M+, 3.2), 125 (100); UV-Vis (dioxane) (λmax / nm (εmax / L mol-1 cm-1)):
234 (25400), 260 (26000), 344 (7200), 451 (3400).
Synthesis of 4-(3,4-dichloro-phenyldiazenyl)-4’-[(4-chlorobenzyl)oxy]
biphenyl (3e)
Spectral study
The structure of these compounds has been investigated on the basis of
UV-visible, IR, 1H NMR and mass spectra.
Compound (3e) was synthesized using the above procedure with 2.28 g
of 4-(3,4-dichloro-phenyldiazenyl)biphenyl-4-ol as azophenol. Yield: 92.1%;
m.p. 160 °C; Anal. Calcd. for C25H17Cl3N2O (%): C 64.19, H 3.66, N 5.99;
Found (%): C 64.07, H 3.59, N 5.81; IR (powder; cm-1): 1560 (N=N), 1409
The electronic spectra, recorded in dioxan, exhibit a R-band due to azo-
group at 432 - 452 nm, a high intensity K-band due to the conjugated system
Ar-N=N-Ar at 338 - 344 nm and a high intensity B-band due to the aromatic
rings at 234 - 263 nm which are in agreement with earlier reports29,30
.
1
(N=N), 1276 (C-O-Casym), 1014 (C-O-C ), 750 (C-Cl); H NMR (60 MHz,
CCl4, δ / ppm): 7.7 (m, 15H, aromatic);sy5m.5 (s, 2H, CH2); MS (m/z, (relative
abundance, %)): (M+, 8.4), 125 (100); UV-Vis (dioxane) (λmax / nm (εmax / L mol-
1 cm-1)): 234 (23200), 261 (30200), 343 (8600), 452 (3800).
The infrared spectra confirm the presence of azo and ether groups in the
structure of compounds 3a-e. The vibration frequency of the N=N31 group
appears at 1400 - 1413 cm-1.
The proofs of the etherification reaction between the hydroxyl group of
azophenol and the 1-chloro-4-(chloromethyl)benzene are:
Antibacterial testing
The antibacterial activity was analyzed against seven microorganisms:
Staphilococcus aureus, Streptococcus pyogenes, Bacillus subtilis, Klebsiella
pneumonia, Salmonela paratyphae, Proteus vulgaris and Escherichia coli. The
tested compounds were dissolved in methanol at a concentration of 0.2% using
chloramphenicol as a standard drug. Tests of different used microorganisms
were carried out by pouring 15 mL sterile Mueller Hinton agar in Petri discs of
9 cm diameter. After solidification, the plates were placed in an incubator at 37
°C for 30 minutes to remove the excessive moisture. Broth culture was streaked
evenly onto medium in three directions using a wooden stick cotton swab. The
plates were aerobically inoculated at 37 °C within 15 minutes. The filter paper
disks with 3a-e compounds, cloramfenicol and methanol were deposed with a
sterile forceps on the plate surface. After 24 hours of incubation at 37 °C, the
diameters of the inhibition zones were measured (including the 6 mm diameter
of the disk) with a rule27. All measurements were performed in triplicate.
-the absence in the IR spectra of the bands characteristic for the hydroxyl
group;
-the presence of absorption bands of the C-O-C newly formed group; thus
spectrum contains an intensive absorption band at 1260 - 1280 cm−1 which can
be assigned to the antisymmetrical valence vibrations of the C-O-C group32-34
and a moderate absorption band due to the symmetrical valence vibrations of
the C-O-C group32-34 at 1013 - 1014 cm-1.
The 1H NMR spectra of all compounds show that the signal of the
CH2 group appears like a singlet at values between δ = 5.0 - 5.5 ppm. The
aromatic protons from the four substituted benzene rings came into resonance
as a multiplet at δ = 7.2 - 7.7 ppm. For 4-(4-methyl-phenyldiazenyl)-4’-[(4-
chlorobenzyl)oxy]biphenyl 3b an additional singlet is present at δ = 2.2 ppm,
corresponding to the methyl group protons34,35
.
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J. Chil. Chem. Soc., 59, Nº 1 (2014)
The fragmentation pattern described in Scheme 2 for 4-phenyldiazenyl-
4’-[(4-chlorobenzyl)oxy]biphenyl 3a, is characteristic for all compounds 3a-e:
pneumonia, Salmonela paratyphae, Proteus vulgaris and Escherichia coli).
Chloramphenicol was used as standard drug and methanol served as control.
Results revealed that in general, all tested compounds possessed good
antibacterial activity against three gram-negative bacteria (Salmonela
paratyphae, Proteus vulgaris and Escherichia coli). The best efficiency at
the tested concentrations was exhibited by 4-(2-chloro-phenyldiazenyl)-
4’-[(4-chlorobenzyl)oxy]biphenyl (3d) against Escherichia Coli and by
4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenyl (3a) against Proteus
vulgaris (Table I). The compounds 3a-e exhibited moderate activity against
Klebsiella pneumonia. Interpretation of antibacterial screening data revealed
that all the tested compound 3a-e showed good inhibition on the growth of
Bacillus subtilis (Table 1). All tested 4-phenyldiazenyl-4’-[(4-chlorobenzyl)
oxy]biphenyls are inactive against Streptococcus pyogenes and Staphylococcus
aureus.
Scheme 2: Fragmentation of 3a under electron impact ionization
According to the literature, scheme 2 shows a major fragmentation of
4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenyl in which the molecular
ion peak at m/z 398 is abundant and the molecule tends to undergo a cleavage
of the O-CH2 bond to give the base peak36.
The results of antibacterial activity of compounds 3a-e were compared
with the standard drug for evaluating their relative percentages of inhibition
(Table 2). The maximum relative percentage of inhibition was exhibited by
3d against Escherichia coli (100%), followed by 3a against Proteus vulgaris
(97.29%).
Antibacterial activity
The antibacterial activity of the investigated 4-phenyldiazenyl-4’-[(4-
chlorobenzyl)oxy]biphenyls 3a-e was done by microdiscs paper diffusion
against three gram-positive bacteria (Staphilococcus aureus, Streptococcus
pyogenes, Bacillus subtilis) and four gram-negative bacteria (Klebsiella
Table 1: Antibacterial activity of 4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenyls 3a-e.
Mean zone of inhibition / mm
Name of organisms
3a
21.66
21.33
23.33
10
3b
20
3c
22.33
28
3d
18.66
30
3e
19.33
25.33
27.33
12.66
17
Chloramphenicol
Methanol
Salmonela paratyphae
Escherichia coli
24
30
30
28
25
20
21
0
0
0
0
0
0
0
24.66
26
Bacillus subtilise
24.33
12
27.66
11.66
16.66
-
Klebsiella pneumonia
Proteus vulgaris
11.33
22.33
-
24.66
-
18
Staphylococcus aureus
Streptococcus pyogenes
-
-
-
-
-
-
-
Table 2: Relative percentage of inhibition of 4-phenyldiazenyl-4’-[(4-chlorobenzyl)oxy]biphenyls 3a-e compared to standard drug chloramphenicol
Relative percentaje of inhibition / %
Name of organisms
3a
3b
3c
3d
3e
Bacillus subtilise
Proteus vulgaris
54.43
97.29
81.45
50.55
12.75
75.11
72.79
69.44
67.56
16.37
65.77
51.84
86.56
87.11
18.36
85
83
44.40
60.45
100
46.24
64.87
71.29
20.44
Salmonela paratyphae
Escherichia coli
Klebsiella pneumonia
17.34
It can be concluded that a combination of biphenyl fragment with azo
group shown promising antibacterial activity and hence they are ideally suited
for further modifications to obtain more efficacious antimicrobial compounds,
in near future. The properties of new antimicrobial substances deserve
further investigation in order to clarify the mode of action at molecular level,
responsible for the activity observed.
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This paper presents the synthesis of five new 4-phenyldiazenyl-4’-
[(4-chlorobenzyl)oxy]biphenyls under Williamson conditions, using the
condensation of different sodium salts of some 4’-phenyldiazenyl-biphenyl-4-
ols with 1-chloro-4-(chloromethyl)benzene.
The formation of azomonoethers was confirmed by the disappearance of
the signal at 3019 - 3030 cm-1 in IR spectra which is typical for hydroxyl group
of azophenols and by the appearance of an intensive absorption band at 1260
- 1280 cm−1 which can be assigned to the antisymmetrical valence vibrations
of the C-O-C group and a moderate absorption band due to the symmetrical
valence vibrations of the C-O-C group at 1013 - 1014 cm-1.
All compounds were subjected to antibacterial activity tests and it can be
concluded that 3a and 3d are microbiological active against Proteus vulgaris
and Escherichia Coli, respectively, and deserve further studies.
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