ISSN 1068-1620, Russian Journal of Bioorganic Chemistry, 2017, Vol. 43, No. 5, pp. 589–594. © Pleiades Publishing, Ltd.

, 2017.

Synthesis and Antimicrobial Activity of Novel 1,4,5-Triphenyl-1H-

Imidazol-[1,2,3]-Triazole Derivatives1
B. Sathish Kumara, B. S. Veenab, P. V. Anantha Lakshmia, 2, L. Kamalaa, and E. Sujathab
aDepartment of Chemistry, University College for Women, Osmania University, Hyderabad, Telangana, 500095 India
bDepartment of Botany, University College of Science, Osmania University, Hyderabad, Telangana, 500007 India
Received December 7, 2016; in final form, March 6, 2017

Abstract—Novel 1-phenyl-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole
derivatives were synthesized by click chemistry reaction and screened for antimicrobial activity against gram-
positive and gram-negative bacterial and fungal species. All the compounds were characterized by 1H and
13
C NMR, IR, and mass spectral data. The results of antibacterial study indicated that 1-(4-nitrophenyl)-4-
((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, 1-(4-(4-((4-(1,4,5-triphenyl-
1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)ethanone, 1-(2,6-dichloro-4-nitrophe-
nyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole, and 1-(2-methoxy-4-
nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole showed appre-
ciable antibacterial activity while 1-(4-fluorophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phe-
noxy)methyl)-1H-1,2,3-triazole, 1-(2,6-dichloro-4-nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-
yl)phenoxy)methyl)- 1H-1,2,3-triazole, and 1-(4-methoxyphenyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-2-
yl)phenoxy)methyl)-1H-1,2,3-triazole emerged as the most potential antifungal agents.

Keywords: click reaction, imidazole, triazole, microbial activity

DOI: 10.1134/S1068162017050120

INTRODUCTION anti-inflammatory [24, 25], anti-HIV [26, 27], anti-

Organic compounds are known to have wide range
of applications in pharmaceutical and agrochemical
products. Compounds that have a particular heterocy-
clic ring system promote activity against a specific
organism based on its effective binding to an enzyme
receptor site. Literature survey revealed that many
compounds bearing five-membered ring system, such
as imidazoles and 1,2,3-triazoles, show significant
biological activity. In compounds containing imidaz-
ole moiety the latter one plays a central role for their
biological activity. Imidazole derivatives were found to
be having diverse activity, including antimicrobial [1–
4], anti-cancer [5, 6], analgesic [7], anti-inflamma-
tory [8–11], antiviral [12], anti-tubercular [13], anti-
convulsant [14], and antidepressant [15] activity. Sim-
ilarly, triazole derivatives have occupied a unique posi-
tion in heterocyclic chemistry due to their specific
chemical and structural properties, which have
received much attention over the past years, and found
wide application in medicinal chemistry [16]. [1,2,3]-
Triazoles play an important role in agrochemicals and
pharmaceuticals,exhibiting antibacterial [17, 18], fun-
gicidal [19–21], antiviral [22], anti-tubercular [23],
1 The article is published in the original.
2 Corresponding author: phone: +91-9849711487;
e-mail:
pvanantha.ou@gmail.com.
proliferative [28], and insecticidal [29] activities.
Based on these findings, our aim was to design and
synthesize novel 1-phenyl-4-((4-(1,4,5-triphenyl-
1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole
derivatives and to screen the diverse activity, i.e. anti-
bacterial and antifungal activities of the newly synthe-
sized compounds, which have linkage between imid-
azole and 1,2,3-triazole moieties. Some of the known
imidazole derivatives (Fig. 1) and 1,2,3-triazole deriv-
atives have been reported to be pharmacologically
active agents, as represented in (Fig. 2).
RESULTS AND DISCUSSION
Chemistry
A series of 1-phenyl-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-[1,2,3]-triazole
derivatives (IIIa–j) was synthesized in three steps
showed in Scheme 1. In the first step, 4-(1,4,5-triphe-
nyl-1H-imidazol-2-yl)phenol(I) was prepared by stir-
ring the mixture of benzil, aniline, p-hydroxybenzal-
dehyde, ammonium acetate, and 10 mol % of iodine
in 5 mL of ethanol at 75°C for 3 h. In the second step,
4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenol (I) was
condensed with propargyl bromide in the presence of
K2CO3 in dimethylformamide (DMF) under reflux

589
590 KUMAR et al.

for 2 h to obtain intermediate 1,4,5-triphenyl-2-(4-
(prop-2-yn-1-yloxy)phenyl)-1H-imidazole (II); inter-
mediate (II) was common to all derivatives being syn-
thesized. In the final step, intermediate (II) was con-
densed with various aromatic azides under click chem-
istry reaction conditions in presence of copper iodide
and dry THF at room temperature for 10–12 h to
result in novel 4-(1,4,5-triphenyl-1H-imidazol-2-
yl)phenoltriazole derivatives (IIIa–j) in quantitative
yields.

Step 1. Synthesis of 4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenol

NH2 CHO Ph N
Ph O OH
NH4OAc, I 2 (10 mol % )
+ + Ph N
EtOH, 75°C
Ph O
OH
I

Step 2. Synthesis of 1,4,5-triphenyl-2-(4-(prop-2-yn-1-yloxy)phenyl)-1H-imidazole (propargylation)

Ph N Ph N
OH K2CO3, DM F O
Ph N + Br Ph N
2 h, Reflux

I II

Step 3. Synthesis of 1-phenyl-4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-

triazole derivatives

Ph N3 N
N N
Ph N
O Dry THF, CuI N
N + O R
Ph RT, 10–12 h
Ph N
R

II
(IIIa)–(IIIj)
(IIIa) R = H (IIIf) R = 4-Br
(IIIb) R = 4-NO 2 (IIIg) R = 4-NO 2, 2,6-Cl
(IIIc) R = 4-Ac (IIIh) R = 4-NO 2, 2-OCH3
(IIId) R = 4-F (IIIi) R = 4-CH 3
(IIIe) R = 4-Cl (IIIj) R = 4-OCH 3

Scheme 1. Synthesis of imidazole-[1,2,3]-triazole derivatives (IIIa–j).

All the derivatives were characterized by 1H and13C
NMR, IR, and ESI-MS spectra. Compounds (IIIa–j)
showed IR absorption bands ranging from 3144 to
3013 cm–1 for aromatic C–H stretching. There were
also absorptions due to C=C and C=N stretchings at
1685–1643 and 1250–1234 cm–1, respectively. In
1H NMR spectra, the presence of singlet resonances
at 5.27–5.11 and 9.17–8.91 ppm were attributed to the
methylene protons attached to oxygen atom and pro-
ton of 1,2,3-triazole ring, respectively, whereas the cor-
responding carbon resonances in the 13C NMR spectra
were observed at 59.8–60.9 and 123.3–123.0 ppm,

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 43 No. 5 2017

 SYNTHESIS AND ANTIMICROBIAL ACTIVITY 591

Cl N
Cl
Cl O
O N
O N
N HN
N N
O
N N

Imidazole based anti fungal drug Imidazole based anti bacterial agent Imidazole based anti fungal drug

Fig. 1. Selected examples of imidazole derivatives with pharmacological activity.

HN HO O
O O
N O
O O Cl NH2 S
N S N H2 N N
O N
N N
OH
S N N O
N
H Cl Cl N O
HO
H2 N
1,2,3-Triazole based drug as an antibiotic used 1,2,3-Triazole based drug as an angiogenesis 1,2,3-Triazole based drug
in the treatment of bacterial infections inhibitor useful in cancer therapy as -lactamase inhibitor

Fig. 2. Selected examples of 1,2,3-triazole derivatives with pharmacological activity.

respectively. All the rest of the protons and carbons C. albicans, and the rest of the compounds showed
resonated at expected regions. moderate activity.

Microbial Studies EXPERIMENTAL

Antibacterial activity. All the synthesized com-
pounds (IIIa–j) were screened in vitro for their anti-
bacterial activity against gram-positive (Staphylococ-
cus aureus, Bacillus subtilis) and gram-negative bacte-
rial strains (Escherichia coli, Klebsiella pneumonia) at
100 µg/mL concentrations. The zone of inhibition (in
mm) was compared with a standard drug ampicillin.
The results are given in the Table 1. Among all, com-
pounds (IIIb), (IIIc), (IIIg), and (IIIh) showed prom-
ising activity against bacterial strains and compounds
(IIIa), (IIId), (IIIe), (IIIf), (IIIi), and (IIIj) showed
moderate zone of inhibition, indicating that com-
pounds with electron-withdrawing substitutions in the
phenyl ring, i.e., –NO2 and –Ac, exhibit the maximal
zone of inhibition. Compounds with substituent R =
F, Cl, Br in the phenyl ring showedmoderate activity.
Antifungal activity. The antifungal activities of syn-
thesized compounds (IIIa–j) were tested against two
pathogenic strains, Aspergillus flavus and Candida
albicans, at 100 µg/mL concentrations. The zone of
inhibition (in mm) was compared with that of a stan-
dard drug clotrimazole. The results are given in the
Table 1. All the compounds showed moderate-to-
good activity against the tested fungal strains. Among
all, compounds (IIId) with flouro substituent and com-
pound (IIIe) with chloro substituent in the ring showed
maximum zone of inhibition and compound (IIIj) with
methoxy substitution in the ring was active against
Materials and Methods
Melting points of all the compounds were recorded
on a Casia-Siamia (VMP-AM) melting point appara-
tus and are uncorrected. IR spectra (ν, cm–1) were
recorded on a 240-C (PerkinElmer, Inc., United
States) FT-IR spectrometer using KBr optics. NMR
spectra were recorded in DMSO-d6 on a DRX-400
(Bruker, Germany) spectrometer with TMS as inter-
nal standard and chemical shifts (δ) expressed in ppm.
Mass spectra were recorded on a VG 7070 H (VG
Micromass) mass spectrometer at 70 eV. All the reac-
tions were monitored on silica gel precoated TLC
plates (Merck, Germany) and spots were visualized
with UV light. Silica gel (100–200 mesh) used for col-
umn chromatography was procured from Merck.
4-(1,4,5-Triphenyl-1H-imidazol-2-yl)phenol (I). A
mixture of benzil (10 mmol), aniline (10 mmol),
p-hydroxybenzaldehyde (10 mmol), ammonium ace-
tate (10 mmol), and iodine (10 mol %) in 5 mL of eth-
anol was stirred at 75°C for 3 h. The completion of
reaction was monitored by TLC. After completion of
the reaction, the reaction mixture was diluted with
water (having small amount of Na2S2O3). The solid
imidazole products that separated out were filtered,
washed with water, and dried. The crude products thus
obtained were subjected to purification by column
chromatography on silica gel (60–120 mesh size)

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 43 No. 5 2017

592 KUMAR et al.

Table 1. Results of antimicrobial activity assay of compounds (IIIa–j) at 100 µg/mL

Zone of inhibition, mm
Compound gram-positive bacteria gram-negative bacteria fungi
S. aeureus B. subtilis E. coli K. pneumonia A. flavus C. albicans
(IIIa) 11 12 10 9 10 9
(IIIb) 14 14 12 12 9 8
(IIIc) 13 14 13 11 9 9
(IIId) 12 14 11 10 12 10
(IIIe) 12 12 11 8 11 9
(IIIf) 9 11 8 8 9 7
(IIIg) 13 12 12 10 10 10
(IIIh) 11 13 8 10 8 7
(IIIi) 9 10 9 8 7 7
(IIIj) 10 11 10 9 10 12
Ampicillin 16 18 17 14 – –
Clotrimazole – – – – 13 12

using 25% ethylacetate in hexane as eluent to yield
compound (I) [30]. Pale yellow solid, yield 88%, mp
175–177°C. 1H NMR: 9.07 (s, 1H, OH), 7.57 (d, J =
7.2 Hz, 2H, Ph), 7.36 (d, J = 8.8 Hz, 2H, Ph), 7.23–
7.18 (m, 9H, Ph), 7.12 (d, J = 6.1 Hz, 2H, Ph), 7.04 (d,
J = 6.0 Hz, 2H, Ph), 6.82 (d, J = 8.8 Hz, 2H, Ph).
1,4,5-Triphenyl-2-(4-(prop-2-yn-1-yloxy)phenyl)-
1H-imidazole (II). Compound (I) (1.0 mol) along with
1.5 mol of potassium carbonate was dissolved in
dimethylformamide (DMF) and solution of propargyl
bromide (1.5 mol) in DMF was added. Reaction mix-
ture was stirred and refluxed to afford crude 1,4,5-
triphenyl-2-(4-(prop-2-yn-1-yloxy)phenyl)-1H-imid-
azole. This crude residue was purified by column
chromatography over silica gel (100–200 mesh) in
15% ethyl acetate in hexane to get compound (II) in
pure state. Pale yellow solid, yield 88%, mp 149–
151°C.1H NMR: 7.59 (d, J = 7.2 Hz, 2H, Ph), 7.37 (d,
J = 8.8 Hz, 2H, Ph), 7.28–7.21 (m, 7H, Ph), 7.19 (s,
2H, Ph), 7.13–7.10 (m, 2H, Ph), 7.06–7.01 (m, 2H,
Ph), 6.84 (d, J = 8.8 Hz, 2H, Ph), 4.66 (s, 2H, CH2),
2.51 (s, 1H, ≡CH). 13C NMR: 157.5, 146.6, 138.5,
134.6, 131.1, 130.7, 130.6, 130.2, 129.9, 129.0, 128.6,
128.5, 128.3, 128.2, 127.9, 127.3, 126.5, 124.1, 114.5,
78.3, 75.6, 55.7. ESI-MS, m/z: 427 (M + 1) observed
for C30H22N2O.
4-(1,4,5-Triphenyl-1H-imidazol-2-yl)phenoltri-
azole derivatives (IIIa–j). Compound (II) (1.0 mmol)
was dissolved in dry THF (10 mL) and catalytic
amount of copper iodide was added. To this, substi-
tuted aromatic azides (1.0 mmol) in dry THF were
added slowly while stirring at room temperature under
nitrogen atmosphere for 12 h. Later, the solvent was
removed under reduced pressure and the residue was
diluted with distilled water and extracted thrice with
dichloromethane. The combined organic layers were
dried over anhydrous Na2SO4 and concentrated to get
the final product (IIIa–j). The crude products were
purified by column chromatography with 30% of ethyl
acetate in hexane.
1-Phenyl-4-((4-(1,4,5-triphenyl-1H-imidazol-2-
yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIa). Yellow
solid, yield 82%, mp 180–183°C. IR: 3074, 1643,
1234, 1033. 1H NMR: 8.93 (s, 1H, =CH triazole ring),
8.10 (d, J = 8.6 Hz, 2H, Ph), 8.02 (d, J = 8.6 Hz, 2H,
Ph), 7.48 (d, J = 7.5 Hz, 2H, Ph), 7.38–7.33 (m, 5H,
Ph), 7.30–7.26 (m, 4H, Ph), 7.26–7.16 (m, 7H, Ph),
7.00 (d, J = 8.7 Hz, 2H, Ph), 5.11 (s, 2H, CH2).
13C NMR: 157.5, 144.3, 144.1, 143.5, 139.3, 136.6,
136.4, 136.3, 134.3, 131.1, 129.8, 129.2, 128.6, 128.5,
128.3, 1282, 128.1, 126.2, 123.2, 119.7, 119.2, 119.1,
114.1, 59.8. ESI-MS, m/z: 546 (M + 1) observed for
C36H27N5O.
1-(4-Nitrophenyl)-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIb).
Yellow solid, yield 91%, mp 185–187°C. IR: 3132,
1660, 1485, 1250. 1H NMR: 9.16 (s, 1H, =CH triazole
ring), 8.47 (d, J = 9.1 Hz, 2H, Ph), 8.24 (d, J = 9.1 Hz,
2H, Ph), 7.48 (d, J = 7.4 Hz, 2H, Ph), 7.38–7.31 (m,
5H, Ph), 7.31–7.28 (m, 3H, Ph), 7.27–7.12 (m, 7H,
Ph), 7.00 (d, J = 8.8 Hz, 2H, Ph), 5.25 (s, 2H, CH2).
13C NMR: 160.1, 146.7, 144.1, 143.6, 139.3, 136.7,
136.5, 136.4, 131.2, 130.1, 129.7, 129.2, 128.7, 128.5,
128.4, 128.3, 128.2, 126.3, 123.2, 123.3, 119.8, 119.3,
119.1, 114.2, 60.0. ESI-MS, m/z: 591 (M + 1) observed
for C36H26N6O3.
1-(4-(4-((4-(1,4,5-Triphenyl-1H-imidazol-2-yl)-
phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)eth-
anone (IIIc). Yellow solid, yield 87%, mp 179–180°C.

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 43 No. 5 2017

 SYNTHESIS AND ANTIMICROBIAL ACTIVITY
IR: 3111, 2970, 1677, 1597, 1250. 1H NMR: 9.08 (s,
1H, =CH triazole ring), 8.17 (d, J = 8.6 Hz, 2H, Ph),
8.09 (d, J = 8.6 Hz, 2H, Ph), 7.50 (d, J = 7.5 Hz, 2H,
Ph), 7.39–7.33 (m, 5H, Ph), 7.31–7.28 (m, 3H, Ph),
7.26–7.16 (m, 7H, Ph), 7.01 (d, J = 8.7 Hz, 2H, Ph),
5.24 (s, 2H, CH2), 2.64 (s, 3H, CH3).13C NMR: 198.9,
157.9, 144.5, 144.1, 143.8, 139.5, 136.8, 136.5, 136.4,
131.1, 131.0, 129.6, 129.1, 128.7, 128.6, 128.4, 128.3,
128.1, 126.3, 123.2, 123.0, 119.8, 119.3, 119.1, 114.3,
60.9, 26.7. ESI-MS, m/z: 588 (M + 1) observed for
C36H26N5O2.
1-(4-Fluorophenyl)-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIId).
Yellow solid, yield 83%, mp 169–171°C. IR: 3111,
2919, 1669, 1527, 1285. 1H NMR: 9.17 (s, 1H, =CH
triazole ring), 8.49 (d, J = 9.1 Hz, 2H, Ph), 8.24 (d,
J = 9.1 Hz, 2H, Ph), 7.5 (d, J = 7.4 Hz, 2H, Ph), 7.38–
7.31 (m, 5H, Ph), 7.31–7.28 (m, 3H, Ph), 7.28–7.13
(m, 7H, Ph), 7.07 (d, J = 8.8 Hz, 2H, Ph), 5.27 (s, 2H,
CH2).13C NMR: 157.9, 144.6, 144.1, 143.7, 139.5,
136.7, 136.5, 136.4, 134.4, 131.1, 130.0, 129.1, 128.7,
128.6, 128.4, 128.3, 128.2, 126.2, 123.1, 119.7, 119.2,
119.1, 114.4, 60.6. ESI-MS m/z: 564 (M + 1) observed
for C36H26FN5O.
1-(4-Chlorophenyl)-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIe).
Paleyellow solid, yield 85%, mp 175–177°C. IR: 3132,
2971, 1679, 1364, 1245. 1H NMR: 9.11 (s, 1H, =CH
triazole ring), 8.45 (d, J = 9.1 Hz, 2H, Ph), 8.24 (d,
J = 9.1 Hz, 2H, Ph), 7.47 (d, J = 7.4 Hz, 2H, Ph),
7.37–7.31 (m, 5H, Ph), 7.31–7.28 (m, 3H, Ph), 7.27–
7.12 (m, 7H, Ph), 7.00 (d, J = 8.8 Hz, 2H, Ph), 5.25 (s,
2H, CH2). ESI-MS, m/z: 580 (M + 1) observed for
C36H26ClN5O.
1-(4-Bromophenyl)-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIf).
Yellow solid, yield 86%, mp 167–169°C. IR spectrum:
3016, 2970, 2223, 1685, 1523, 1248. 1H NMR: 9.14 (s,
1H, =CH triazole ring), 8.47 (d, J = 9.1 Hz, 2H, Ph),
8.24 (d, J = 9.1 Hz, 2H, Ph), 7.47 (d, J = 7.4 Hz, 2H,
Ph), 7.37–7.31 (m, 5H, Ph), 7.31–7.28 (m, 3H, Ph),
7.27–7.12 (m, 7H, Ph), 7.01 (d, J = 8.8 Hz, 2H, Ph),
5.26 (s, 2H, CH2). ESI-MS, m/z: 624 (M + 1)
observed for C36H26BrN5O.
1-(2,6-Dichloro-4-nitrophenyl)-4-((4-(1,4,5-
triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-
triazole (IIIg). Yellow solid, yield 90%, mp 170–
172°C. IR: 3111, 2970, 1677, 1597, 1246. 1H NMR:
9.01 (s, 1H, =CH triazole ring), 8.23 (s, 2H, Ph), 7.46
(d, J = 7.4 Hz, 2H, Ph), 7.39–7.30 (m, 5H, Ph), 7.29–
7.25 (m, 3H, Ph), 7.21–7.11 (m, 7H, Ph), 7.03 (d, J =
8.8 Hz, 2H, Ph), 5.23 (s, 2H, CH2).13C NMR: 157.9,
146.5, 144.1, 143.8, 139.4, 136.7, 136.5, 136.4, 131.2,
130.0, 129.6, 129.1, 128.7, 128.6, 128.4, 128.3, 128.1,
126.3, 123.4, 123.3, 120.1, 119.4, 119.1, 114.3, 58.9.
ESI-MS, m/z: 659 (M + 1) observed for C36H24Cl2N6O3.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
593
1-(2-Methoxy-4-nitrophenyl)-4-((4-(1,4,5-triph-
enyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-tri-
azole (IIIh). Yellow solid, yield 88%, mp 155–157°C.
IR: 3144, 2970, 1666, 1342, 1250. 1H NMR: 8.91(s,
1H, =CH triazole ring), 8.15 – 8.05 (m, 3H, Ph), 7.50
(d, J = 7.5 Hz, 2H, Ph), 7.34 (t, J = 6.0 Hz, 5H, Ph),
7.30–7.17 (m, 10H, Ph), 7.01 (d, J = 8.7 Hz, 2H, Ph),
5.24 (s, 2H, CH2), 3.61 (s, 3H, CH3). ESI-MS, m/z:
621 (M + 1) observed for C37H28N6O4.
1-(p-Tolyl)-4-((4-(1,4,5-triphenyl-1H-imidazol-
2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIi). Yellow
solid, yield 82%, mp 171–173°C. IR: 3016, 2970, 1685,
1248. 1H NMR: 9.06 (s, 1H, =CH triazole ring), 8.17
(d, J = 8.6 Hz, 2H, Ph), 8.09 (d, J = 8.6 Hz, 2H, Ph),
7.50 (d, J = 7.5 Hz, 2H, Ph), 7.39–7.33 (m, 5H, Ph),
7.31–7.28 (m, 3H, Ph), 7.26–7.16 (m, 7H, Ph), 7.00
(d, J = 8.7 Hz, 2H, Ph), 5.23 (s, 2H, CH2), 2.30 (s,
3H, CH3).13C NMR: 157.8, 144.5, 144.0, 143.8, 139.4,
136.7, 136.5, 136.4, 134.4, 131.1, 130.0, 129.1, 128.7,
128.6, 128.4, 128.3, 128.1, 126.3, 123.0, 119.8, 119.2,
119.6, 114.3, 60.8, 21.1. ESI-MS, m/z: 560 (M + 1)
observed for C37H29N5O.
1-(4-Methoxyphenyl)-4-((4-(1,4,5-triphenyl-1H-
imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazole (IIIj).
Yellow solid, yield 85%, mp 180–182°C. IR: 3013,
2853, 1675, 1249, 1115. 1H NMR: 9.08 (s, 1H, =CH
triazole ring), 8.17 (d, J = 8.6 Hz, 2H, Ph), 8.09 (d,
J = 8.6 Hz, 2H, Ph), 7.50 (d, J = 7.5 Hz, 2H, Ph),
7.38–7.33 (m, 5H, Ph), 7.30–7.14 (m, 10H, Ph), 7.01
(d, J = 8.7 Hz, 2H, Ph), 5.24 (s, 2H, CH2), 3.32 (s,
3H, CH3). 13C NMR: 157.8, 144.3, 144.2, 143.7, 139.5,
136.8, 136.5, 136.4, 131.2, 129.9, 129.6, 129.1, 128.7,
128.6, 128.4, 128.3, 128.1, 126.3, 123.3, 123.1, 119.9,
119.3, 119.1, 114.2, 60.7, 26.3. ESI-MS, m/z: 576
(M + 1) observed for C37H29N5O2.
Biological Assay
Antibacterial assay. All the synthesized compounds
were evaluated for their in vitro antibacterial activity
against gram-positive bacteria S. aureus and B. subtilis
and gram-negative bacteria E. coli and K. pneumonia.
The bacterialcultures were grown in nutrient agar
media and sub cultured for the better growth (log-
phase cultures) in a liquid nutrient broth medium and
further inoculation onto the Petri plates for the exper-
iments. The broth cultures were diluted with sterilized
saline to bring the final size of inoculums approxi-
mately to 105–106 CFU/mL. The compounds were
diluted in DMSO for biological assays. The bacterial
culture inoculums were placed on the media and incu-
bated at 37°C for 24–48 h along with the chemical
disks dipped and placed over the media. The zones of
bacterial growth inhibition were measured, using the
diameter of the zone (mm) as a unit to measure the
antibacterial activity. All the experiments were carried
out in triplicates. The results were compared with the
Vol. 43 No. 5 2017
594 KUMAR et al.
activity of the standard antibiotic ampicillin
(100 µg/mL). For disk diffusion method, the test
compound was introduced onto the disk and then
allowed to dry. Once the disk was completely saturated
with the test compound, it was introduced onto the
upper layer of the medium containing the bacterial
inoculum. The Petri dishes were incubated overnight
at 37°C for 24 h.
Antifungal assay. The antifungal activity of synthe-
sized compounds was tested against two pathogenic
fungi, A. flavus and C. albicans, by the poison plate
technique. Test compounds were dissolved in DMSO
(10 mL) before mixing with potato dextrose agar
medium (PDA, 90 mL). The final concentration of
compounds in the medium was maintained to be
100 µg/mL. Above-mentioned speciesof fungi were
incubated in PDA at 25 ± 1°C for 3–4 days to get good
mycelium growth for antifungal assay; then, a mycelia
disk approximately 0.45 cm in diameter cut from the
culture medium was picked up with a sterilized inocu-
lation needle and inoculated in the center of a PDA
plate. The inoculated plates were incubated at 25 ±
1°C for 5 days. DMSO in sterilized distilled water was
used as control, while clotrimazole was used as stan-
dard for all the treatments; three replicates were per-
formed. The radial growth of the fungal colonies was
measured on the fourth day, and the data were statisti-
cally analyzed. The in vitro inhibition effects of the test
compounds on the fungi were calculated by the given for-
mula: CV = A – B/A, where A represents the diameter of
fungi growth on untreated PDA, B, the diameter of fungi
on treated PDA, and CV, the rate of inhibition.
ACKNOWLEDGMENTS
We thank DST-FIST Program of India
(SR/FST/CSI-213/2010) for infrastructural facilities.
B.S. Kumar would like to acknowledge UGC-New
Delhi, India, for Junior Research Fellowship. We also
thank Director of CFRD, Osmania University,
Hyderabad, for providing spectral analysis facilities.
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