Synthesis and molecular docking studies of novel 2-phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one derivatives

Article abstract of DOI:10.1134/S1070363217050279

2-Phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one derivatives were synthesized by click chemistry reactions. Exploration of molecular interaction of the obtained compounds, performed through molecular docking studies with

Full text of DOI:10.1134/S1070363217050279

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 5, pp. 1057–1063. © Pleiades Publishing, Ltd., 2017.
Synthesis and Molecular Docking Studies
of Novel 2-Phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-1
yl)methoxy]benzylidene}oxazol-5(4H)-one Derivatives
B. Sathish Kumar and P. V. Anantha Lakshmi*
Department of Chemistry, University College for Women, Osmania University, Hyderabad, Telangana, 500007 India
*
e-mail: pvanantha.ou@gmail.com
Received December 28, 2016
Abstract—2-Phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one
derivatives were synthesized by click chemistry reactions. Exploration of molecular interaction of the obtained
compounds, performed through molecular docking studies with α-glucosidase, revealed the high docking
scores (LibDock) in the range of 135.056–126.164 as compared to acarbose (136.345).
Keywords: 1,2,3-triazoles, click reaction
DOI: 10.1134/S1070363217050279
, oxazolones, α-glucosidase, molecular docking
Diabetes mellitus (DM) is also a growing health
problem and according to WHO reports, around
analgesic [5], anticancer [6], antidiabetic [7], anti-
inflammatory [8], neuroleptic [9], anti-obesity [10],
sedative [11] and important intermediates in the
preparation of several chemicals including peptides
[12], amino acids [13], some heterocyclic precursors
[14, 15], as well as coupling and photosensitive
devices for proteins [16]. They exhibit promising
photophysical and photochemical activities [17, 18]
and as pH sensors [19]. On the other hand 1,2,3-tri-
azole derivatives show significant biological activities
such as anti-inflammatory [20], antibacterial [21],
antiproliferative [22], antiviral [23], anti-HIV [24, 25],
fungicidal [26], and insecticidal [27, 28].
2
50 million people are currently living with diabetes
and this number is expected to be more than
66 million by 2030 [1]. Treatments of type 2 diabetes
3
mellitus (T2DM) include improvement of insulin
sensitivity or reducing the rate of carbohydrate absorp-
tion from the gastrointestinal tract. α-Glucosidase is a
membrane-bound enzyme at the epithelium of the
small intestine and plays a key role in carbohydrate
digestion. Inhibition of α-glucosidase leads to the
delay or reduction of increased postprandial blood
glucose levels. Thus, one of the therapeutic approaches
for treating diabetes is the inhibition of the enzyme α-
glucosidase which delays carbohydrate digestion. α-
Glucosidase inhibitors have been proposed as a
potential therapeutic target for drug discovery in the
treatment of T2DM. Since many decades, active
heterocyclic compounds are one of the main topic of
interest for the medicinal chemists as it displays a
number of pharmacological activities. The compounds
having 4-benzylidene-2-phenyloxazol-5(4H)-one (azlac-
tone) moiety are potential intermediates for the
synthesis of various bioactive heterocycles utilized in
the asymmetric synthesis of amino acids and for the
homologation of carboxylic acids. Azlactones are
associated with interesting wide spectrum of biological
activities, such as antibacterial [2, 3], antifungal [4],
Biological potencies of 4-benzylidene-2-phenyl-
oxazol-5(4H)-one and 1,2,3- triazole pharmacophores
prompted us to synthesize a series of novel 2-phenyl-4-
{
4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]benzyl-
idene}oxazol-5(4H)-one derivatives and perform
in silico molecular docking studies.
2-Phenyl-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)meth-
oxy]benzylidene}oxazol-5(4H)-ones were synthesized
in three steps. In the first step, 4-hydroxybenzaldehyde
or 4-hydroxy-3-methoxybenzaldehyde reacted with
propargylbromide in the presence of K CO in dry
2
3
DMF under reflux to afford the corresponding 4-(prop-
-yn-1-yloxy)benzaldehyde derivatives 1a or 1b
Scheme 1). In the next step, sodium acetate catalyzed
2
(
reaction of 1 with N-benzoylglycin 2 in acetic an-
hydride resulted in 2-phenyl-4-[4-(prop-2-yn-1-yloxy)-
benzylidene]oxazol-5(4H)-ones 3a or 3b (Scheme 2).
1
The text was submitted by the authors in English.
1
057

1
058
SATHISH KUMAR, ANANTHA LAKSHMI
CHO
Scheme 1.
CHO
Scheme 2.
O
H
O
N
OH
+
Br
R
+
R
OH
O
a, 1b
CHO
1
2
K CO , DMF
2
3
1
h, reflux
R
O
R
O
1
a, 1b
AC
2
O, NaOAC
O
O
N
R = H (a), OCH
3
(b).
Reflux, 2 h
In the final step, intermediate 3 was subjected to cyclo-
addition with various substituted azides under click
chemistry reaction conditions in the presence of CuI as
a catalyst in dry THF for 12 hours to furnish novel
3
a, 3b
R = H (a), OCH (b).
3
4
-{4-[(-1H-1,2,3-triazol-4-yl)methoxy]benzylidene}-2-
phenyloxazol-5(4H)-ones 4a–4i in quantitative yields
(
Scheme 3).
due to C=C and C=N stretching at 1559–1541 and
–
1
1
455–1428 cm , respectively.
Structure of compounds 4a–4i was confirmed by
1
13
1
H, C NMR, IR, and ESI-MS spectral data. In the H
Exploration of molecular interaction of the title
NMR spectra of 4 there were singlet resonances at 5.81–
.21 and 9.23–8.47 ppm corresponding to the
compounds was performed through molecular docking
studies using Discovery Studio 2.1 software. To study
the molecular interaction of the compounds,
crystallographic data of α-glucosidase (PDB: 2QMJ)
was retrieved from Protein Data Bank. Retrieved
crystal structure of human α-glucoamylase was
cleaned and hydrogen atoms were added. All the
heteroatoms were removed before docking study.
5
methylene protons attached to the oxygen atom and the
proton of 1,2,3-triazole ring, respectively, whereas the
corresponding carbon resonances in the C NMR spectra
were observed at 52.7–52.1 and 121.9–120.6 ppm,
respectively. Rest all the protons and carbons resonated
at expected regions. The IR spectra contained the
absorption bands ranging from 3093 to 3070 cm for
aromatic C–H stretching, 2977 to 2933 cm for
aliphatic C–H stretching. There were also absorptions
13
–
1
–
1
The molecular docking study of 4-{4-[(-1H-1,2,3-tri-
azol-4-yl)methoxy]benzylidene}-2-phenyloxazol-5(4H)-
Scheme 3.
O
R1
O
R
O
2
N
O
R −N , CuI
R1
3
O
N
O
N
N N
THF, room temperature,
1
0−12 h
3
a, 3b
(a), 4-CH
6 5
(h), C H
4
a−4i
1
2
4
(
: R = H, R = 4-NO
2
C
6
H
4
3
C(O)C
6
H
4
(b), 4-CH C H
3 6 4
(c), 4-OCH C H
3 6 4
(d), 4-FC H
6 4
(e), C H CH (f), 4-FC H CH
6 5 2 6 4 2
1
2
g); R = OCH
3
, R = 4-NO
2
C
6
H
4
(i).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

SYNTHESIS AND MOLECULAR DOCKING STUDIES
(b)
1059
(
a)
(
c)
(d)
(
e)
(f)
Receptor-ligand hydrogen bonds and bumps of compounds (a) 4a, (b) 4b, (c) 4f, (d) 4g, (e) 4h, and (f) acarbose with active site
residues of α-glucosidase (PDB: 2QMJ).
ones 4a–4i with α-glucosidase revealed the high
docking scores (LibDock) and binding affinities in the
range of 135.056–126.164 as compared to acarbose,
showed good dock score. These results indicate that
most of the compounds bound within the binding site
pocket of doxorubicin similar binding pattern with
binding site amino acid residues. These results indicate
that the compounds are bound well within the binding
site pocket of acarbose and the almost similar binding
pattern was identified. The significant docking
score on the respective targets infers that these
1
36.345 (see the table and figure). All the synthesized
compounds used in the molecular docking studies have
shown good docking score. Compound 4h showed the
close dock score as acarbose, a known antidiabetic
drug. On the other hand, compounds 4a, 4b, 4f, and 4g
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1
060
SATHISH KUMAR, ANANTHA LAKSHMI
Dock score (LibDock) and ligand interaction data of the compounds 4a–4i
LibDock Interacting amino
H-Bond
distance
Compound
Interacting atoms
Donor Acceptor
score
acids
2
0
20
4
a
135.056
TRP539,
TRP441
A:TRP539:HE1–4a: N1
A:TRP539:HE1–4a: N
A:TRP441:CZ2–4a: H
HE1
HE1
CZ2
N
N
H
2.488000
2.381000
2.212000
9
19
45
45
1
9
19
44
40
4
b
135.382
129.751
ASP542,
ARG526,
ASP203
A:ASP542:HN1–4b: N
HN1
CA
HH22
N
H
H
2.154000
2.172000
1.676000
4
4
A:ASP203:CA–4b: H
A:ARG526:HH22–4b: H
40
2
0
20
19
48
45
4
c
ASP542,
TRP441,
ASP203
A:ASP542:HN1–4c: N1
HN1
HN1
CH2
CA
N
N
H
H
2.250000
2.480000
2.151000
2.200000
9
A:ASP542:HN1–4c: N
48
A:TRP441:CH2–4c: H
45
A:ASP203:CA–4c: H
2
0
20
19
51
51
4
d
128.995
ARG526,
TRP441
A:ARG526:HH12–4d: N1
A:ARG526:HH12–4d: N
HH12
HH12
CZ2
N
N
H
H
2.195000
2.467000
1.803000
2.207000
9
51
A:TRP441:CZ2–4d: H
51
A:TRP441:CH2–4d: H
CH2
2
0
20
19
45
4
e
126.568
132.721
ASP542,
ASP203
A:ASP542:HN1–4e: N1
A:ASP542:HN1–4e: N
A:ASP203:CA–4e: H
HN1
HN1
CA
N
N
H
2.366000
2.422000
2.122000
9
4
5
1
9
19
20
51
38
4
f
TRP539,
YR299,
TRP441
A:TRP539:HE1–4f: N2
A:TRP539:HE1–4f: N
HE1
HE1
CB
N
N
H
H
2.036000
2.420000
2.142000
2.189000
0
5
1
A:TYR299:CB–4f: H
38
A:TRP441:CZ2–4f: H
CZ2
2
0
20
19
4
g
130.515
137.085
ARG526
A:ARG526:HH12–4g: N1
A:ARG526:HH12–4g: N
HH12
HH12
N
N
2.251000
2.109000
9
2
0
20
8
4
h
TYR299,
ASP542,
ILE328
A:TYR299:HH–4h: N
HH
OD1
CD1
N
2.490000
2.403000
2.028000
8
A:ASP542:OD1–4h: C4
C
2
42
A:ILE328:CD1–4h: H
H
1
9
19
20
49
4
i
126.164
136.345
ASP542,
TRP441
A:ASP542:HN1–4i: N2
HN1
HN1CH2
N
N
H
2.282000
2.173000
2.147000
0
A:ASP542:HN1–4i: N
49
A:TRP441:CH2–4i: H
45
Acarbose
HIS600,
ARG526,
ASP542,
TRP539,
ASP203
acr: H –A:HIS600:NE2
H45
HH12
H56
HH12
HH12
HE1
H57
H54
H67
H56
H77
NE2
2.322000
2.245000
2.313000
2.217000
2.418000
2.375000
1.876000
1.600000
2.174000
1.469000
1.944000
9
A:ARG526:HH12–acr:O9
acr:H56–A:ASP542:OD2
A:ARG526:HH12–acr:O4
A:ARG526:HH12–acr:O17
A:TRP539:HE1–acr:O11
acr:H57–A:HIS600:O
acr:H54–A:ASP203:OD1
acr:H67–A:HIS600:CD2
acr:H56–A:ARG526:HH12
acr:H77–A:ASP203:OD1
O
OD2
4
O
1
1
7
1
O
O
O
OD1
CD2
HH12
OD1
compounds can be potential lead candidates for anti-
diabetic drugs.
penetration, aqueous solubility, hepatotoxicity, cyto-
chrome P450 2D6 binding) were also calculated to
check the compliance of the tested compounds with the
standard range. The pharmacokinetic profiles of all the
compounds were predicted by means of Discovery
Different chemical descriptors for the pharmaco-
kinetics properties (absorption level, blood-brain barrier
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

SYNTHESIS AND MOLECULAR DOCKING STUDIES
1061
Studio 2.1 ADMET models. The aqueous solubility
prediction (defined in water at 25°C) indicated that all
the compounds are soluble in water. All the com-
pounds are found to be non-inhibitors of cytochrome
P450 2D6 (CYP2D6), which is one of the important
enzymes involved in drug metabolism. During
ADMET screening, the predictive hepatotoxicity was
observed for the candidate compounds in comparison
to acarbose.
Synthesis of 2-phenyl-4-[4-(prop-2-yn-1-yloxy)-
benzylidene]oxazol-5(4H)-one derivatives (3). A mix-
ture of O-propargylated benzaldehyde 1 (33 mmol),
fused sodium acetate (33 mmol) and benzoyl glycine
(33 mmol) in acetic anhydride (83 mmol) was refluxed
with stirring for 2 h (the reaction progress was
monitored by TLC). After cooling, the mixture was
treated with water (10 mL), filtered and washed with
water. The product was purified by recrystalisation
from absolute ethanol.
In summary, a series of 2-phenyl-4-{4-[(1-phenyl-
2
-Phenyl-4-[4-(prop-2-yn-1-yloxy)benzylidene]-
1H-1,2,3-triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-
oxazol-5(4H)-one (3a). Yield 90%, mp 140–142°C.
one hybrids was synthesized. For all the compounds
molecular docking studies were performed with α-
glucosidase and pharmacokinetic profiles (ADMET
screening) predicted by means of Discovery Studio
1
H NMR spectrum, δ, ppm: 8.24–8.12 m (4H), 7.59 t
(
7
1H, J = 7.4 Hz), 7.52 d (2H, J = 7.7 Hz), 7.20 s (1H),
.07 d (2H, J = 8.9 Hz), 4.76 s (2H), 2.57 s (1H). C
1
3
NMR spectrum, δ , ppm: 167.8, 162.7, 159.9, 134.4,
2
.1. Molecular docking studies revealed that com-
C
1
7
33.0, 131.5, 131.5, 128.9, 128.2, 127.3, 125.8, 115.3,
7.8, 76.1, 55.9.
pounds 4a, 4b, 4f–4h were potent inhibitors of human
α-glucosidase.
Synthesis of 2-phenyl-4-{4-[(1-phenyl-1H-1,2,3-
EXPERIMENTAL
triazol-4-yl)methoxy]benzylidene}oxazol-5(4H)-one
derivatives (4a–4i). To a solution of 4-benzyl-
ideneoxazol-5(4H)-one 3 (3.0 mmol) in dry THF
10 mL) were sequentially added catalytic amount of
copper iodide and a solution substituted azide
3.0 mmol) in dry THF. The mixture was stirred at
Melting points of all the compounds were deter-
mined on Casia-Siamia (VMP-AM) melting point
apparatus and were uncorrected. IR spectra were
registered on a Perkin–Elmer FT-IR 240 spectrometer
using KBr pellets. NMR spectra were recorded on a
Bruker Avance 300 MHz instrument in CDCl or
DMSO-d solution using TMS as an internal standard.
Mass spectra were registered on a VG Micro mass
model 7070H instrument. All the reactions were
monitored by TLC using precoated Merck silica gel
plates visualized with UV light. Silica gel (100–
(
(
room temperature under nitrogen atmosphere for 12 h,
and then the solvent was removed under reduced
pressure. The residue was diluted with distilled water
and extracted thrice with ethyl acetate. The combined
organic layers were dried over anhydrous Na SO and
3
6
2
4
concentrated to get the product. The crude product was
purified by column chromatography eluting with ethyl
acetate–hexane (1:9).
2
00 mesh) used for column chromatography was
procured from Merck.
4
-(4-{[1-(4-Nitrophenyl)-1H-1,2,3-triazol-4-yl]-
Synthesis of 4-(prop-2-yn-1-yloxy)benzaldehyde
derivatives (1). To a solution of 4-hydroxybenz-
4-hydroxy-3-methoxybenzaldehyde
23 mmol) and potassium carbonate (22 mmol) in
methoxy}benzylidene)-2-phenyloxazol-5(4H)-one
–
1
(
3
4a). Yield 86%, mp 160–162°C. IR spectrum, ν, cm :
1
aldehyde
(
1
or
088, 2933, 1672, 1559, 1428. H NMR spectrum, δ,
ppm: 9.23 s (1H), 8.47 d (2H, J = 8.8 Hz), 8.34 d (2H,
J = 9.1 Hz), 8.26 d (2H, J = 8.8 Hz), 8.12 d (2H, J =
0 mL of dry DMF was slowly added propargyl-
bromide (23 mmol) while stirring. The reaction
mixture was stirred at room temperature for 2 h and
then extracted with ethyl acetate to afford crude
O-propargyl benzaldehyde. The latter was purified by
column chromatography eluting with 15% ethyl
acetate in hexane.
7
7
.4 Hz), 7.72 t (1H, J = 6.9 Hz), 7.64 t (2H, J =
.4 Hz), 7.36 s (1H), 7.27 d (2H, J = 8.5 Hz), 5.41 s
1
3
(
2H). C NMR spectrum, δ , ppm: 168.9, 161.0,
C
1
1
5
59.5, 149.7, 149.2, 145.2, 135.7, 132.0, 130.3, 128.7,
28.4, 127.9, 127.4, 126.5, 123.8, 121.7, 118.6, 110.3,
2.7. Mass spectrum (ESI-MS): m/z 468 [M + 1].
C H N O .
2
5
17
5
5
4
-(Prop-2-yn-1-yloxy)benzaldehyde (1a). Yield
1
9
(
4
2%, mp 76–78°C. H NMR spectrum, δ, ppm: 9.99 s
1H), 7.87 d (J = 7.6 Hz, 2H), 7.10 d (J = 7.6 Hz, 2H),
.53 s (2H), 2.57 s (1H).
4-(4-{[1-(4-Acetylphenyl)-1H-1,2,3-triazol-4-yl]-
methoxy}benzylidene)-2-phenyloxazol-5(4H)-one
(4b). Yield 85%, mp 158–160°C. IR spectrum, ν, cm :
–
1
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

1
062
SATHISH KUMAR, ANANTHA LAKSHMI
1
13
3
072, 2929, 1670, 1557, 1450. H NMR spectrum, δ,
C NMR spectrum, δ , ppm: 161.0, 159.7, 159.5,
C
ppm: 9.23 s (1H), 8.47 d (2H, J = 8.8 Hz), 8.34 d (2H,
J = 9.1 Hz), 8.26 d (2H, J = 8.8 Hz), 8.12 d (2H, J =
149.8, 149.2, 144.1, 135.7, 132.0, 131.1, 130.4, 129.4,
128.7, 128.4, 128.1, 127.9, 123.9, 121.1, 118.7, 55.9,
52.7. Mass spectrum (ESI-MS): m/z 437 [M + 1].
C H N O .
7
7
.4 Hz), 7.72 t (1H, J = 6.9 Hz), 7.64 t (2H, J =
.4 Hz), 7.36 s (1H), 7.27 d (2H, J = 8.5 Hz), 5.41 s
2
6
20
4
3
1
3
(
2H), 2.51 s (3H). C NMR spectrum, δ , ppm: 196.9,
C
4
-(4-{[1-(4-Fluorobenzyl)-1H-1,2,3-triazol-4-yl]-
1
1
1
4
68.9, 161.1, 159.6, 149.8, 149.2, 144.1, 139.3, 136.3,
31.1, 130.4, 129.9, 129.5, 128.3, 121.9, 121.0, 119.7,
18.7, 110.5, 52.5, 26.7. Mass spectrum (ESI-MS): m/z
65 [M + 1]. C H N O .
methoxy}benzylidene)-2-phenyloxazol-5(4H)-one
–1
(
3
4g). Yield 88%, mp 148–150°C. IR spectrum, ν, cm :
1
093, 2970, 1671, 1558, 1429. H NMR spectrum, δ,
2
7
20
4
4
ppm: 8.76 s (1H), 8.28 d (2H, J = 8.8 Hz), 8.21 d (2H,
J = 8.1 Hz), 8.14 d (2H, J = 8.9 Hz), 7.98 d (2H, J =
7.4 Hz), 7.71 t (1H, J = 6.9 Hz), 7.62 t (2H, J =
7.4 Hz), 7.39 s (1H), 7.26 d (2H, J = 8.5 Hz), 5.26 s
(2H), 4.98 s (2H). Mass spectrum (ESI-MS): m/z 455
[M + 1]. C H FN O .
2
-Phenyl-4-(4-{[1-(p-tolyl)-1H-1,2,3-triazol-4-yl]-
methoxy}benzylidene)oxazol-5(4H)-one (4c). Yield
–
1
8
1
2%, mp 155–156°C. IR spectrum, ν, cm : 2928,
1
672, 1558, 1429. H NMR spectrum, δ, ppm: 9.11 s
(
8
(
7
1H), 8.37 d (2H, J = 8.8 Hz), 8.21 d (2H, J = 9.1 Hz),
.19 d (2H, J = 8.8 Hz), 8.11 d (2H, J = 7.4 Hz), 7.66 t
1H, J = 6.9 Hz), 7.51 t (2H, J = 7.4 Hz), 7.27 s (1H),
.15 d (2H, J = 8.5 Hz), 5.32 s (2H), 2.24 s (3H). Mass
spectrum (ESI-MS): m/z 437 [M + 1]. C H N O .
2
6
19
4
3
4
-(3-Methoxy-4-{[1-(4-nitrophenyl)-1H-1,2,3-tri-
azol-4-yl]methoxy}benzylidene)-2-phenyloxazol-5(4H)-
one (4h). Yield 88%, mp 145–160°C. IR spectrum, ν,
2
6
20
4
4
–1
1
cm : 2971, 1672, 1559, 1455. H NMR spectrum, δ,
ppm: 8.47 d (2H, J = 8.8 Hz), 8.35 s (1H), 8.26 d (2H,
J = 8.8 Hz), 8.12 d (2H, J = 7.4 Hz), 7.72 s (1H), 7.68–
7.49 m (3H), 7.36 s (1H), 7.31–7.29 m (1H), 7.26 d
4
-(4-{[1-(4-Methoxyphenyl)-1H-1,2,3-triazol-4-
yl]methoxy}benzylidene)-2-phenyloxazol-5(4H)-one
–
1
(
4d). Yield 85%, mp 158–160°C. IR spectrum, ν, cm :
1
13
2
8
9
7
976, 1676, 1559, 1428. H NMR spectrum, δ, ppm:
.81 s (1H), 8.31 d (2H, J = 8.8 Hz), 8.18 d (2H, J =
.1 Hz), 8.12 d (2H, J = 8.8 Hz), 8.80 d (2H, J =
.4 Hz), 7.62 t (1H, J = 6.9 Hz), 7.39 t (2H, J = 7.4
(1H, J = 7.1 Hz), 5.40 s (2H), 3.71 s (3H). C NMR
spectrum, δ , ppm: 168.8, 160.9, 159.9, 149.9, 149.0,
C
143.3, 142.3, 135.8, 132.2, 131.7, 131.0, 130.6, 129.5,
129.4, 128.3, 127.6, 121.6, 120.0, 118.7, 110.5, 54.1,
52.1. Mass spectrum (ESI-MS): m/z 498 [M + 1].
C H N O .
Hz), 7.31 s (1H), 7.26 d (2H, J = 8.5 Hz), 5.81 s (2H),
3
1
.79 s (3H). Mass spectrum (ESI-MS): m/z 453 [M +
2
6
19
5
6
]. C H N O .
2
6
20
4
4
4-{3-Methoxy-4-[(1-phenyl-1H-1,2,3-triazol-4-yl)-
4
-(4-{[1-(4-Fluorophenyl)-1H-1,2,3-triazol-4-yl]-
methoxy]benzylidene}-2-phenyloxazol-5(4H)-one
–
1
methoxy}benzylidene)-2-phenyloxazol-5(4H)-one
4e). Yield 85%, mp 145–146°C. IR spectrum, ν, cm :
(4i). Yield 86%, mp 148–149°C. IR spectrum, ν, cm :
–
1
1
(
3087, 2973, 1672, 1526, 1429. H NMR spectrum, δ,
1
2
8
9
7
7
977, 1672, 1541, 1428. H NMR spectrum, δ, ppm:
.98 s (1H), 8.47 d (2H, J = 8.8 Hz), 8.34 d (2H, J =
.1 Hz), 8.26 d (2H, J = 8.8 Hz), 8.12 d (2H, J =
.4 Hz), 7.72 t (1H, J = 6.9 Hz), 7.64 t (2H, J =
.4 Hz), 7.16 s (1H), 7.27 d (2H, J = 8.5 Hz), 5.43 s
ppm: 8.47 d (2H, J = 8.8 Hz), 8.35 s (1H), 8.26 d (2H,
J = 8.8 Hz), 8.12 d (2H, J = 7.4 Hz), 7.72 s (1H), 7.68–
7.49 m (3H), 7.36 s (1H), 7.31–7.29 m (1H), 7.26 d
1
3
(1H, J = 7.1 Hz), 5.40 s (2H), 3.71 s (3H). C NMR
spectrum, δ , ppm: 168.9, 161.0, 159.7, 159.5, 149.8,
C
1
3
(
2H). C NMR spectrum, δ , ppm: 168.9, 161.1,
149.2, 144.1, 135.8, 132.0, 131.1, 130.4, 129.4, 128.7,
128.3, 128.1, 127.9, 123.8, 121.1, 118.7, 110.4, 54.1,
52.3. Mass spectrum (ESI-MS): m/z 453 [M + 1].
C H N O .
C
1
1
5
59.8, 159.4, 149.3, 146.7, 145.2, 143.7, 140.6, 132.0,
30.3, 128.4, 127.5, 125.4, 122.1, 120.6, 118.7, 110.4,
2.2. Mass spectrum (ESI-MS): m/z 441 [M + 1].
2
6
20
4
4
C H FN O .
2
5
17
4
3
ACKNOWLEDGMENTS
4
-{4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-
benzylidene}-2-phenyloxazol-5(4H)-one (4f). Yield
Authors thank to DST-FIST Program of India (SR/
–
1
8
2
7
7
6%, mp 170–172°C. IR spectrum, ν, cm : 3070,
977, 1674, 1559, 1428. H NMR spectrum, δ, ppm:
.63 s (1H), 7.53–7.49 m (2H), 7.33–7.30 m (2H), 7.29–
.26 m (3H), 7.24 s (1H), 7.22–7.18 m (2H), 7.16–7.10
FST/CSI-213/2010) for infra structural facilities and
the Director, CFRD, Osmania University, Hyderabad
for providing spectral analysis. One of the authors, B.
Sathish Kumar, is grateful to UGC-New Delhi for
Research Fellowship.
1
m (3H), 6.91–6.87 m (2H), 5.21 s (2H), 5.12 s (2H).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 5 2017

SYNTHESIS AND MOLECULAR DOCKING STUDIES
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