One-pot synthesis of bis(4,5-diphenylimidazol-2-yl-phenyl)glycols and evaluation of their antimicrobial activity

Article abstract of DOI:10.1134/S107036321503024X

Abstract A new series of bis(4,5-diphenylimidazol-2-yl-phenyl)glycols were synthesized by reaction of bis(formylphenyl)glycols with benzil/benzoin and ammonium acetate in presence of iodine/acetic acid in ethanol. All newly synthesized compounds were char

Full text of DOI:10.1134/S107036321503024X

ISSN 1070-3632, Russian Journal of General Chemistry, 2015, Vol. 85, No. 3, pp. 673–678. © Pleiades Publishing, Ltd., 2015.
One-Pot Synthesis
of Bis(4,5-diphenylimidazol-2-yl-phenyl)glycols
1
and Evaluation of Their Antimicrobial Activity
G. Linga Goud, S. Ramesh, D. Ashok, and V. Prabhakar Reddy
Department of Chemistry, Osmania University, Hyderabad, 500 007 India
e-mail: ashokdou@gmail.com
Received November 13, 2014
Abstract—A new series of bis(4,5-diphenylimidazol-2-yl-phenyl)glycols were synthesized by reaction of bis-
(
formylphenyl)glycols with benzil/benzoin and ammonium acetate in presence of iodine/acetic acid in ethanol.
1
13
All newly synthesized compounds were characterised by IR, H, C NMR, and MS data and tested for
antimicrobial and antifungal activity.
Keywords: bis-aldehyde, bis-imidazole, ammonium acetate, antimicrobial activity
DOI: 10.1134/S107036321503024X
INTRODUCTION
Based on the above data we have carried out
synthesis of the title compounds by using iodine
catalyst as presented in Scheme 2.
Importance of imidazole and its derivatives in
pharmacology and organic synthesis is well docu-
mented [1–3]. Various substituted imidazoles possess
anti-allergic, analgesic [4], antiparasitic [5], anti-
epileptic [6], anti-inflammatory [7], anticancer [8,9],
antimycobacterial, and antifungal activities [10].
Substituted imidazoles are core molecules in biological
systems such as biotin, histamine and histidine. Bis-
imidazoles act as desensitizing agents, protein
analogues [11], and artificial multi-dentate ligands in
binding metal ions [12].
Antibacterial activity. All synthesized compounds
were screened in vitro for their antibacterial activity
against gram +ve bacterial strains Staphylococcus
aureus (ATCC-9144), Bacillus cereus (ATCC-11778)
and gram –ve bacterial strains Escherichia coli
(
ATCC-8739), Proteus vulgaris (ATCC-29213) by the
cup-plate agar diffusion method at 25, 50, and 100 µg/mL
concentrations. The zone of inhibition (in mm) was
compared with the standard drug Ampicillin (Table 2).
All newly synthesized compounds were active against
the tested strains. Compounds Vg, Vj, Vm, and Vo
were more potent or of same activity as the standard
drug.
RESULTS AND DISCUSSION
As a part of our ongoing study of synthesis of
biodynamic heterocycles [13, 14] we synthesized new
bis-imidazole derivatives from bis-benzaldehydes
IIIa–IIIo (Scheme 1) and benzil in the presence of
ammonium acetate and iodine in ethanol with high
yields. The preliminary study of the reaction of benzil/
benzoin under various catalytic conditions such as
acetic acid and iodine in ethanol (Table 1) was carried
out. The results revealed that the reaction of bis-
benzaldehyde with benzil in presence of iodine in
ethanol gave significantly improved yields of products
compared to other conditions.
Antifungal activity. All synthesized compounds
were screened in vitro for antifungal activity against
Aspergillus Niger (ATCC-9029), Candida albicans
Table 1. Preliminary tests of mixtures substrate-catalyst
Product
Substrate
Benzil
Catalyst Time, min Yield, %
AcOH
210
15
65–75
90–95
62–70
80–85
Benzil
I
2
Va
Benzoin
Benzoin
AcOH
I2
240
20
1
The text was submitted by the authors in English.
6
73

6
74
LINGA GOUD et al.
Scheme 1.
HO
O
O
n
DMF, K CO
2
3
Br
Br
CHO +
OHC
CHO
8
0oC, 8 h
n
Ia−Ic
IIa−IIe
IIIa−IIIo
O
O
n
OHC
CHO
IIIa−IIIo
O
O
n
Iodine (5 mol %)
N
N
EtOH, NH OAc
4
O
N
H
N
H
Va−Vo
O
IV
n = 2–6.
Scheme 2.
N
N
H
O
O
n
H
N
N
N
N
N
N
H
H
O
O
n
Va−Ve
Vf−Vj
N
N
H
O
O
n
N
N
H
Vk−Vo
n = 2–6.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 3 2015

ONE-POT SYNTHESIS OF BIS(4,5-DIPHENYLIMIDAZOL-2-YL-PHENYL)GLYCOLS
Table 2. Antibacterial activity of compounds Va–Vo
675
Zone of inhibition, mm
S. aureus
B. cereus
E. coli
P. vulgaris
Product
(ATCC-9144)
(ATCC-11778)
(ATCC-8739)
(ATCC- 29213)
2
5
50
10
9
100
25
5
50
7
100
8
25
10
11
6
50
12
14
6
100
14
16
7
25
50
10
9
100
11
Va
9
11
11
12
13
11
12
15
12
14
16
14
13
15
12
15
12
9
8
Vb
8
10
10
8
4
5
7
11
12
13
11
12
15
12
14
16
14
13
15
12
15
14
Vc
11
10
10
11
13
10
12
13
12
11
12
10
12
10
3
5
6
10
10
8
11
10
10
11
13
10
12
13
12
11
12
10
12
11
Vd
6
7
7
11
9
13
10
9
15
12
10
10
13
12
15
10
10
14
16
16
17
Ve
4
6
7
Vf
8
4
6
8
9
8
Vg
10
10
10
11
11
10
10
9
6
7
8
8
10
12
11
13
10
8
10
10
10
11
11
10
10
9
Vh
5
6
8
11
10
12
8
Vi
4
5
5
Vj
6
7
8
Vk
5
7
9
Vl
4
6
8
7
Vm
Vn
6
7
9
10
10
11
14
12
14
13
15
4
5
7
Vo
9
5
7
9
9
Ampicillin
7
11
13
15
9
(
ATCC-2091), Aspergillus foetidus (NCIM-0505), and
Candida rogosa (ATCC-9849). The zone of inhibition
in mm) was compared with standard drugs Ampho-
(10 mmol), ammonium acetate (20 mmol), 2,3,4-
[(2,3,4-formylphenoxy)alkoxy]benzaldehydes (5 mmol)
and iodine (5 mol) in ethanol (2 mL) was refluxed for
15–20 min. Progress of the reaction was monitored by
TLC (Silica gel, aluminium sheets 60 F , Merck).
Upon completion of the process the reaction mixture
was poured in water. The precipitated solid was
filtered off, washed with water, dried and purified by
column chromatography to yield title compounds Va–
Vo (90–95 %) (Scheme 2).
(
tericin-B and Clotrimazole (Table 3). The products
demonstrated moderate to high activity against the
tested fungal strains. Compounds Vg, Vj, Vm, and Vo
were more potent than the standard drugs. Compounds
Vd and Vh were inactive against Candida albicans.
2
54
EXPERIMENTAL
Compound Va (n = 2). Yield 93%, mp 245–247°C.
Melting points were determined in open glass
capillary tube on a Gallen-Kamp MFB-595 apparatus.
The IR spectra were recorded on a Perkin-Elmer FT-
–
1
IR spectrum, ν, cm : 1555 (C=N), 1660 (C=C), 3435
1
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 4.63 s
3
1
(4H, 2OCH
Ar-H), 10.49 br.s (2H, NH). С NMR spectrum, δ
ppm: 65.2, 112.4, 119.3, 120.3, 121.5, 122.6, 127.0,
27.9, 128.2, 128.8, 129.6, 144.6, 152.6. M 651 [M +
2
), 6.78–7.60 m (26H, Ar-H), 8.44 d.d (2H,
IR-8400s using samples in KBr disks. The H NMR
1
3
13
,
С
(
400 MHz) and C NMR (100 MHz) spectra were
recorded on Bruker Avance II 400 spectrometer in
1
CDCl and DMSO-d with TMS as the internal
3
6
+
H] . Found, %: C 81.12; H 5.16; N 8.52. C H N O .
44
34
4
2
standard. Mass spectra were measured on SHIMADZU
LCMS 2020 mass spectrometers. Elemental analysis
was performed on a Perkin Elmer CHN-2400 analyzer.
Calculated, %: C 81.21; H 5.27; N 8.61.
Compound Vb (n = 3). Yield 92%, mp 245–247°C.
–
1
IR spectrum, ν, cm : 1565 (C=N), 1672 (C=C), 3431
1
Bis(4,5-diphenylimidazol-2-yl-phenyl)glycols (Va–
Vo) (general procedure). A mixture of benzil/benzoin
(N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.20–1.25
3
m (2H, C–CH –C), 4.25 t (4H, 2OCH ), 6.88 d.d (2H,
2
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 3 2015

6
76
LINGA GOUD et al.
Table 3. Antifungal activity of compounds Va–Vo
Zone of inhibition, mm
A. niger
A. foetidus
C. albicans
C. rogosa
Product
(ATCC-9021)
(NCIM-505)
(ATCC-2091)
(ATCC-9849)
2
5
50
7
100
25
7
50
8
100
9
25
4
50
6
100
7
25
50
8
100
9
Va
Vb
Vc
Vd
Ve
5
8
7
6
7
7
7
6
4
7
6
4
3
6
4
5
6
7
9
5
8
9
7
9
5
4
6
8
5
5
7
6
8
7
7
8
9
–
–
–
8
9
6
6
7
8
5
6
8
7
8
Vf
4
6
5
4
6
5
4
6
4
5
8
9
6
7
8
8
5
8
6
9
7
10
8
3
7
–
4
8
6
3
5
4
8
8
9
5
9
7
10
–
5
8
7
4
8
6
7
8
8
9
6
7
6
9
8
5
9
7
8
9
9
9
8
8
7
10
8
Vg
Vh
Vi
6
8
7
8
–
5
5
4
5
6
5
6
6
Vj
7
8
8
9
10
8
9
11
8
10
8
Vk
Vl
7
9
6
7
7
6
8
7
8
8
4
6
8
Vm
Vn
Vo
7
9
8
9
10
10
10
11
14
8
8
10
10
10
9
5
7
8
9
5
5
7
9
9
9
10
10
10
11
12
11
Amphotericin B
Clotrimazole
10
11
13
13
9
10
12
11
10
Ar-H), 6.93–6.98 m (4H, Ar-H), 7.05–7.16 m (4H,
Ar-H), 7.25–7.28 m (8H, Ar-H), 7.30–7.36 m (8H, Ar-
5.56; N 8.22. C H N O . Calculated, %: C 81.39; H
46 38 4 2
5.64; N 8.25.
1
3
H), 7.50 d.d (2H, Ar-H), 10.98 br.s (2H, NH).
С
Compound Vd (n = 5). Yield 91%, mp: 208–210°C.
NMR spectrum, δ , ppm: 30.6, 68.2, 112.4, 114.3,
–1
С
IR spectrum, ν, cm : 1550 (C=N), 1662 (C=C), 3432
1
1
5
5
19.3, 120.4, 123.2, 124.8, 125.2, 126.9, 127.8, 128.6,
44.6, 154.6. M 665 [M + H] . Found, %: C 81.22; H
1
(
N–H). Н NMR spectrum (DMSO), δ, ppm: 1.63–1.70
+
m (2H, C–CH –C), 1.89–1.99 m [4H, 2(C–CH –C)],
2
2
.38; N 8.40. C H N O . Calculated, %: C 81.30; H
4
5
36
4
2
4
.08 t (4H, 2OCH ), 7.05–7.36 m (26H, Ar-H), 7.96
2
.46; N 8.43.
13
d.d (2H, Ar-H), 11.73 br.s (2H, NH). С NMR
spectrum, δ , ppm: 22.3, 28.3, 67.9, 112.5, 114.5,
С
Compound Vc (n = 4). Yield 90%, mp 240–241°C.
–
1
119.0, 120.6, 126.5, 127.0, 127.4, 128.0, 128.8, 129.8,
IR spectrum, ν, cm : 1545 (C=N), 1665 (C=C), 3432
+
1
143.3, 155.4. M 693 [M + H] . Found, %: C 81.40; H
(
[
N–H). Н NMR spectrum (CDCl ), δ, ppm: 2.00 t
3
5
5
.76; N 8.02. C H N O . Calculated, %: C 81.48; H
47 40 4 2
4H, 2(C–CH –C)], 4.20 t (4H, 2OCH ), 6.95 d.d (2H,
2
2
.82; N 8.09.
Compound Ve (n = 6). Yield 95%, mp: 225–227°C.
Ar-H), 7.12–7.15 m (4H, Ar-H), 7.25–7.28 m (4H,
Ar-H), 7.27–7.32 m (8H, Ar-H), 7.33–7.38 m (8H,
1
3
–1
1
Ar-H), 7.96 d.d (2H, Ar-H), 10.85 br.s (2H, NH). С
IR, ν, cm : 1548 (C=N), 1660 (C=C), 3434 (N–H). Н
NMR spectrum (DMSO), δ, ppm: 1.63–1.70 m [4H,
2(C–CH –C)], 1.89–1.99 m [4H, 2(C–CH –C)], 4.08 t
NMR spectrum, δ , ppm: 29.5, 67.3, 112.5, 114.4,
С
1
1
19.5, 120.8, 122.6, 126.2, 126.8, 127.9, 128.2, 129.5,
2
2
+
43.2, 154.5. M 679 [M + H] . Found, %: C 81.32; H
(4H, 2OCH ), 7.05 d.d (2H, Ar-H), 7.08–7.36 m (24H,
2
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 3 2015

ONE-POT SYNTHESIS OF BIS(4,5-DIPHENYLIMIDAZOL-2-YL-PHENYL)GLYCOLS
677
1
3
1
Ar-H), 7.96 d.d (2H, Ar-H), 11.73 br.s (2H, NH). С
(N–H). Н NMR spectrum (CDCl
m [4H, 2(C–CH
4.37 t (4H, 2OCH
(22H, Ar-H), 7.70 d.d (4H, Ar-H), 11.50 br.s (2H,
3
), δ, ppm: 1.63–1.70
NMR spectrum, δ , ppm: 24.3, 28.2, 67.8, 112.5,
14.6, 119.0, 120.2, 120.6, 122.5, 126.6, 127.4, 128.7,
29.8, 143.2, 155.4. M 707 [M + H] . Found, %: C
1.50; H 5.92; N 7.89. C H N O . Calculated, %: C
1.56; H 5.99; N 7.93.
Compound Vf (n = 2). Yield 94%, mp 240–241°C.
IR spectrum, ν, cm : 1552 (C=N), 1665 (C=C), 3432
2
–C)], 1.89-1.99 m [4H, 2(C–CH
2
–C)],
С
1
1
8
8
2
), 6.92 d (2H, Ar-H), 7.21–7.52 m
+
1
3
NH). С NMR spectrum, δ
, ppm: 21.3, 28.0, 66.9,
С
48
42
4
2
112.5, 114.4, 119.1, 121.6, 126.6, 127.0, 127.4, 128.5,
28.8, 129.6, 142.8, 158.0. M 707 [M + H] . Found, %:
C 81.52; H 5.97; N 7.90. C48
C 81.56; H 5.99; N 7.93.
+
1
–
1
H N O . Calculated, %:
42 4 2
1
(
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 4.37 s
3
Compound Vk (n = 2). Yield 95%, mp 230–231°C.
4H, 2OCH ), 6.92 d (2H, Ar-H), 7.21–7.55 m (22H,
2
–
1
1
3
IR spectrum, ν, cm : 1552 (C=N), 1665 (C=C), 3432
Ar-H), 7.66 d.d (4H, Ar-H), 12.35 br.s (2H, NH). С
1
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 4.32 s
NMR spectrum, δ , ppm: 65.6, 112.6, 119.5, 120.5,
21.6, 122.5, 127.0, 127.8, 128.6, 128.7, 129.3, 144.0,
52.5. M 651 [M + H] . Found, %: C 81.12; H 5.16; N
.52. C H N O . Calculated, %: C 81.21; H 5.27; N
3
С
(
4H, 2OCH ), 6.93 d.d (4H, Ar-H), 7.23–7.70 m (20H,
Ar-H), 8.01 d.d (4H, Ar-H), 11.68 br.s (2H, NH). С
NMR spectrum, δ , ppm: 66.5, 114.6, 122.7, 127.0,
28.2, 128.3, 128.5, 129.0, 135.5, 136.2, 158.6. M 651
M + H] . Found, %: C 81.12; H 5.16; N 8.52.
1
1
8
8
2
1
3
+
С
4
4
34
4
2
1
[
.61.
+
Compound Vg (n = 3). Yield 95%, mp 260–261°C.
IR spectrum, ν, cm : 1552 (C=N), 1665 (C=C), 3428
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.95–2.20
m (2H, C–CH –C), 4.32 t (4H, 2OCH ), 6.90 d (4H,
Ar-H), 7.21–7.46 m (22H, Ar-H), 7.50 d.d (2H, Ar-H),
0.85 br.s (2H, NH). С NMR spectrum, δ , ppm:
0.5, 68.3, 112.6, 114.8, 119.8, 120.9, 124.5, 125.0,
26.9, 127.5, 128.8, 129.8, 145.7, 158.6. M 655 [M +
C H N O . Calculated, %: C 81.21; H 5.27; N 8.61.
4
4
34
4
2
–
1
1
Compound Vl (n = 3). Yield 91%, mp 253–255°C.
(
3
–
1
IR spectrum, ν, cm : 1548 (C=N), 1663 (C=C), 3429
2
2
1
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.91–2.27
3
1
3
m (2H, C–CH –C), 4.22 t (4H, 2OCH ), 7.06 d.d (4H,
Ar-H), 7.15–7.88 m (22H, Ar-H), 8.00 d.d (2H, Ar-H),
2.52 br.s (2H, NH). С NMR spectrum, δ , ppm:
31.8, 66.0, 113.6, 122.7, 123.9, 127.1, 128.1, 128.4,
29.0, 135.6, 136.0, 158.7. M 665 [M + H] . Found, %:
C 81.26; H 5.40; N 8.38. C H N O . Calculated, %:
C 81.30; H 5.46; N 8.43.
2
2
1
3
1
С
1
3
1
С
+
H] . Found, %: C 81.28; H 5.38; N 8.40. C H N O .
45
36
4
2
+
1
Calculated, %: C 81.30; H 5.46; N 8.43.
Compound Vh (n = 4). Yield 91%, mp 225–228°C.
IR spectrum, ν, cm : 1548 (C=N), 1662 (C=C), 3430
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.92 t
4H, 2(C–CH –C)], 4.29 t (4H, 2OCH ), 6.93 d (4H,
Ar-H), 6.99–7.50 m (22H, Ar-H), 7.70 d.d (2H, Ar-H),
0.89 br.s (2H, NH). С NMR spectrum, δ , ppm:
9.0, 67.9, 112.6, 114.6, 119.8, 120.5, 122.9, 124.5,
26.8, 127.9, 128.6, 129.0, 144.2, 156.5. M 679 [M +
4
5
36
4
2
–
1
Compound Vm (n = 4). Yield 90%, mp 210–213°C.
1
(
[
–1
3
IR spectrum, ν, cm : 1552 (C=N), 1661 (C=C), 3430
2
2
1
(
[
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.90 t
3
4H, 2(C–CH –C)], 4.22 t (4H, 2OCH ), 7.08 d.d (4H,
Ar-H), 7.19–7.32 m (3H, Ar-H), 7.35–7.45 m (10H,
Ar-H), 7.59–7.62 m (7H, Ar-H), 8.01 d.d (4H, Ar-H),
0.52 br.s (2H, NH). С NMR spectrum, δ , ppm:
0.8, 65.0, 113.0, 122.5, 123.6, 127.2, 128.2, 128.5,
29.1, 134.9, 136.2, 157.9. M 679 [M + H] . Found, %:
1
3
2
2
1
2
1
С
13
1
3
1
+
С
H] . Found, %: C 81.32; H 5.56; N 8.22. C H N O :
4
6
38
4
2
Calculated, %: C 81.39; H 5.64; N 8.25.
+
Compound Vi (n = 5). Yield 90%, mp 235–237°C.
C 81.32; H 5.56; N 8.22. C46
C 81.39; H 5.64; N 8.25.
H N O . Calculated, %:
38 4 2
–
1
IR spectrum, ν, cm : 1554 (C=N), 1665 (C=C), 3436
1
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.47–1.54
3
Compound Vn (n = 5). Yield 93%, mp 250–253°C.
m (2H, C–CH –C), 1.68–1.80 m [4H, 2(C–CH –C)],
–1
2
2
IR spectrum, ν, cm : 1552 (C=N), 1658 (C=C), 3430
1
4
(
.37 t (4H, 2OCH ), 6.92 d (4H, Ar-H), 7.20–7.50 m
2
(
N–H). Н NMR spectrum (CDCl ), δ, ppm: 1.45–1.49
3
22H, Ar-H), 7.75 d.d (2H, Ar-H), 11.89 br.s (2H,
m (2H, C–CH –C), 1.90–2.10 m [4H, 2(C–CH –C)],
2
2
1
3
NH). С NMR spectrum, δ , ppm: 23.0, 28.5, 67.0,
С
4
.31 t (4H, 2OCH ), 7.02 d.d (4H, Ar-H), 7.20–7.30 m
2
1
1
12.5, 114.8, 119.0, 120.5, 126.5, 127.0, 127.5, 128.7,
(
12H, Ar-H), 7.40–7.50 m (8H, Ar-H), 8.00 d.d (4H,
+
1
3
28.9, 129.8, 145.3, 158.6. M 693 [M + H] . Found, %:
Ar-H), 10.52 br.s (2H, NH). С NMR spectrum, δС,
ppm: 22.6, 31.0, 65.2, 113.3, 122.5, 123.6, 127.2,
C 81.45; H 5.79; N 8.02. C H N O . Calculated, %:
4
7
40
4
2
C 81.48; H 5.82; N 8.09.
1
27.5, 128.5, 129.2, 134.0, 136.2, 157.8. M 693 [M +
+
Compound Vj (n = 6). Yield 94%, mp 180–182°C.
H] . Found, %: C 81.46; H 5.78; N 8.04. C46
Calculated, %: C 81.48; H 5.82; N 8.09.
H N O .
40 4 2
–
1
IR spectrum, ν, cm : 1550 (C=N), 1664 (C=C), 3431
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 3 2015

6
78
LINGA GOUD et al.
Compound Vo (n = 6). Yield 93%, mp 205–207°C.
Laping, N.J., J. Med. Chem., 2002, vol. 45, p. 999.
–
1
IR spectrum, ν, cm : 1552 (C=N), 1658 (C=C), 3430
2. Kawasaki, I., Sakaguchi, N., Khadeer, A.,Yamashita, M.,
1
(
N–H). Н NMR spectrum (DMSO), δ, ppm: 1.63–1.67
and Ohta, S., Tett., 2006, vol. 62, p. 10182.
m [4H, 2(C–CH –C)], 1.90–2.20 m [4H, 2(C–CH –C)],
2
2
3. Matsuoka, Y., Ishida, Y., Sasaki, D., and Saigo, K.,
4
.31 t (4H, 2OCH ), 7.08 d.d (4H, Ar-H), 7.19–7.32 m
Tett., 2006, vol. 62, p. 8199.
2
(
12H, Ar-H), 7.45–7.55 m (8H, Ar-H), 8.01 d.d (4H,
4
5
. Ucucu, U., Karaburun, N.G., and Iskdag, I., Il Farmaco,
2001, vol. 56, p. 285.
1
3
Ar-H), 10.52 br.s (2H, NH). С NMR spectrum, δС,
ppm: 22.8, 29.3, 63.2, 113.3, 122.5, 123.6, 127.1,
1
. Hernandez Nunez, E., Tlahuext, H., Moo Puc, R.,
Torres Gomez, H., Reyes Martinez, R., Cedillo Rivera, R.,
Nava Zuazo, C., and Navarrete Vazquez, G., Eur. J.
Med. Chem., 2009, vol. 44, p. 2975.
27.8, 128.6, 129.5, 134.2, 136.2, 157.6. M 707 [M +
+
H] . Found, %: C 81.52; H 5.94; N 7.88. Calculated,
: C H N O : C 81.56; H 5.99; N 7.93.
%
4
8
42
4
2
6
. Karakurt, A., Dalkara, S., Ozalp, M., Ozbey, S., Kendi, E.,
and Stables, J.P., Eur. J. Med. Chem., 2001, vol. 36,
p. 421.
CONCLUSIONS
We have carried out one-pot synthesis of new
substituted derivatives of imidazole, i.e. bis(4,5-
diphenylimidazol-2-yl-phenyl)glycols (Va–Vo), with
high yields. All synthesized compounds demonstrated
high antimicrobial activity.
7
8
. Lombardino, J.G. and Wiseman, E.H., J. Med. Chem.,
1974, vol. 17, p. 1182.
. Suzuki, F., Kuroda, T., Tamura, T., Soichiro, S.,
Ohmori, K., and Ichikawa, S., J. Med. Chem., 1992,
vol. 35, p. 2863.
9
. Bhatnagar, A., Sharma, P.K., and Kumar, N., Int. J.
Pharm. Tech. Res., 2011, vol. 3, p. 268.
ACKNOWLEDGMENTS
1
0. Banfi, E., Scialino, G., Zampieri, D., Mamolo, M.G.,
Vio, L., ,Ferrone, M., Fermeglia, M., Paneni, M.S., and
Pricl, S.J., J. Anti. Chem., 2006 vol. 58 p. 76.
Authors are grateful to the Head, Department of
Chemistry, and Director, Central Facilities for
Research and Development (CFRD), Osmania
University, Hyderabad for providing laboratory
facilities. One of the authors GLG is grateful to UGC,
New Delhi for award of JRF.
1
1
1. Mallik, S., Johnson, R.D., and Arnold, F.H., J. Am.
Chem. Soc., 1994, vol. 116, p. 8902.
2. Fei, B.L., Sun, W.Y., Zhang, Y.A., Yu, K.B., and
Tang, W.X., J. Chem. Soc Dalton Trans., 2000,
vol. 2000, p. 2345.
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