Synthesis, characterization, and antimicrobial activity of novel (E)-1-(aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones

Article abstract of DOI:10.1134/S107036321606027X

The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88% yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benzaldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, ¹H NMR, ¹³C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial activity by the agar disc diffusion method.

Full text of DOI:10.1134/S107036321606027X

ISSN 1070-3632, Russian Journal of General Chemistry, 2016, Vol. 86, No. 6, pp. 1405–1411. © Pleiades Publishing, Ltd., 2016.
Synthesis, Characterization, and Antimicrobial Activity
of Novel (E)-1-(Aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-
1
1
,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones
a
a
a
b
N. J. P. Subhashini , Ch. Sravanthi , K. Sravanthi , and Shivaraj
a
Department of Chemistry, University College of Technology, Osmania University, Hyderabad, 500007 India
e-mail: njsubhashini@yahoo.co.in
b
Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007 India
Received November 30, 2015
Abstract—The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-
dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88%
yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benz-
1
aldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, H
13
NMR, C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial
activity by the agar disc diffusion method.
Keywords: antimicrobial activity, propargyl bromide, substituted azides, 4-hydroxy-3,5-dimethoxybenzaldehyde
DOI: 10.1134/S107036321606027X
INTRODUCTION
Triazoles and their derivatives, as important
pharmacological heterocyclic nuclei, have been
extensively studied. In recent years, 1,2,3-triazole
chemistry developed very rapidly due to the discovery
of various biologically active triazole derivatives. The
1,2,3-triazole system synthesized using “click
chemistry” [22, 23] is applied in various areas as an
interesting biologically active component. To increase
the bacterial resistance, it is necessary to develop new
antibacterial agents with novel structures and activities
and this remains the primary goal of researches.
In the realm of biochemistry, chalcones have been
efficiently studied as antimicrobial [1], antileishmanial
2], antimalarial [3], antifungal [4], antiviral [5], anti-
[
inflammatory [6], cytotoxic [7], antitumour [8],
nematicidal [9] antioxidant [10], anti-invasive [11],
and anticancer [12–14] agents. Also, nitrogen-
containing heterocyclic compounds play an important
role in agrochemistry and pharmaceutics. The five-
membered nitrogen heterocycles are the important
components of biological systems. Among them, 1,2,3-
triazoles and their derivatives are of considerable
interest because they possess a wide range of
biological properties, such as anti-HIV [15],
antiallergic [16], antifungal [17], antiviral [18], and
antimicrobial activity [19], which makes them
pharmaceutically important molecules. They are stable
to reduction and oxidation and to hydrolysis in acidic
and basic conditions, i.e., are aromatic heterocycles. In
addition, 1,2,3-triazoles are stable toward light,
moisture, oxygen, and body metabolism. Also, these
compounds are widely applied as photosensitizers,
dyes [20] and commercially applied as anticorrosive
agents [21].
The structures of certain drugs containing the 1,2,3-
triazole ring system are shown in Scheme 1.
Therefore, the goal of this study is the synthesis,
using “click chemistry,” of novel chalcones containing
the 1,2,3-triazole ring system. The compounds syn-
thesized show good antibacterial activity as compared
to standard agents. Data on the antibacterial and
antifungal activities are collected in Tables 1 and 2,
respectively.
EXPERIMENTAL
All chemicals were of the lab Research grade and
were purchased from Avra, Sigma-Aldrich, and Merck.
Melting points were measured in open capillaries on an
electronic melting point apparatus. The purity of the
1
The text was submitted by the authors in English.
1
405

1
406
SUBHASHINI et al.
Scheme 1.
NH2
Cl
O
H
N
O
H
N
O
H N
N
N
S
2
S
HO
O
N
N
Cl
Cl
N
N
N
NH
O
N
O
H N
O
N
2
COOH
COOH
Anticancer compound
arboxyamidotriazole (CAI)
Tazobactum
anti baterialdrug
Cefatrizine
cephalosporin antibiotic
compounds was determined by thin-layer chromato-
graphy (TLC) with a Silica Gel GF254 sheet (MERCK)
under UV light visualization. The compounds were
purified by column chromatography (silica gel 60–
(DMSO, 100 MHz) spectra were recorded on a Bruker
Biospin Avance-III spectrometer. Mass spectra were
measured on a QSTAR XL Hybrid LC/MS/MS
quadrupole electrospray ionization time-of-flight mass
spectrometer.
1
20 mesh). The UV-Vis spectra were recorded on an
OPTIZEN 3220 spectrophotometer and FT-IR spectra
were measured on a SHIMADZU IR435 spectrophoto-
Preparation of compounds 3a, 3b, 4a, 4b, 6a–6l is
shown in Scheme 2.
1
13
meter. H NMR (DMSO/CDCl , 400 MHz) and C NMR
3
RESULTS AND DISCUSSION
Table 1. Antibacterial activity of the synthesized compounds
General procedure for synthesizing chalcones
3a, 3b. A mixture of 3,5-di-benzyloxy acetophenone 1
and substituted aromatic aldehydes 2a, 2b in ethanolic
Antibacterial activity, zone of inhibition,
mm
Gram-negative
bacteria
Gram-positive
bacteria
Compounds
Table 2. Antifungal activity of the synthesized compounds
Antifungal activity, radius of fungal
mycelia, mm
Compounds
S. Rolfsii
40
M. Phaseolina
Ampicillin
5
10
3
4
7
3
5
5
9
5
4
7
6
8
5
5
3
11
9
6
9
9
10
5
Control
40
17
22
24
15
13
11
16
20
20
25
30
22
20
Streptomycin
Fluconazole
5
6
a
5
4
6a
6b
6c
6d
6e
6f
25
6
b
4
8
5
7
15
6
c
5
5
6
8
13
6
d
12
9
12
7
10
6
10
6
14
6
e
12
6
f
7
7
5
6
15
6
g
6
6
7
4
6g
6h
6i
14
6
h
6
6
5
5
13
6
i
11
8
10
6
14
5
11
8
40
6
j
6j
40
6
k
5
8
6
7
6k
6l
30
6
l
6
5
4
6
32
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016

SYNTHESIS, CHARACTERIZATION, AND ANTIMICROBIAL ACTIVITY
1407
Scheme 2.
R
O
O
H
O
NaOH, MeOH
room temperature, 72 h
+
R
Step 1
H CO
OCH3
H CO
OCH3
3
3
OH
OH
3
a, 3b
1
2a, 2b
Propargylbromide
DMF, room temperature, 6 h
Step 2
O
R
R
O
Step 3
DMF, CuSO , 48−72 h
4
Sodium ascorbate, room temperature
N3
H CO
OCH3
3
O
H CO
OCH3
3
O
R1
N
5a−5h
N
N
R1
4a, 4b
6
a−6l
1
1
1
1
R = 4-Br, 3-OMe (2a, 2b); R = 4-Br, R = H (6a); R= 4-Br, R = 4-NO
CH (6d); R =4-Br, R = 3-Cl (6e); R = 4-Br, R = 4-CO–CH (6f); R = 4-Br, R = 3-COOH (6g); R = 3-OMe, R = 4-NO
3 3 2
6h); R = 3-OMe, R = 3-Cl (6i); R = 3-OMe, R = 3-COOH (6j); R = 3-OMe, R = 4-COOH (6k); R = 3-OMe, R = 4-CO–
2
(6b); R = 4-Br, R = 2-OMe (6c); R =4-Br, R = 4-
1
1
1
1
1
1
1
1
(
3
CH (6l). Experimental conditions: (Step 1) NaOH, MeOH, reaction time 72 h, stirring; (Step 2) propargyl bromide, DMF,
reaction time 6 h, (Step 3) substituted azides, DMF, CuSO4, and sodium ascorbate, stirring for 48–72 h.
KOH was stirred at room temperature till the product
was obtained. Completion of the reaction was
monitored by TLC. The residues were treated with a
General procedure for the synthesis of different
substituted azides 5a–5h. To a mixture of different
substituted amines (1 equiv.) and concentrated HCl, a
solution of sodium nitrite (1.5 equiv.) was added
dropwise and then a solution of sodium azide
(1.5 equiv.) was slowly introduced. The mixtures were
kept stirring about 2–3 h. The reaction course was
monitored by TLC. After the reactions were complete,
1
0% HCl in ice cold water to obtain the corresponding
chalcones 3a, 3b in good yield. The solid was filtered,
washed with water and then with methanol. The
compounds were purified by column chromatography.
The yield of the products was within 80–85% (Scheme 3).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016

1
408
SUBHASHINI et al.
Scheme 3.
A
R1
R2
R1
R2
+
CH3
OHC
O
O
A = 60% KOH, ethanol, room temperature.
products were extracted 3 times into ethyl acetate, the
combined organic layers were washed with brine, dried
over anhydrous Na SO , and concentrated under
1-one (6a). Reaction time 57 h, yield 76%, mp 172–
–1
175°C. IR spectrum, ν, cm : 1121, 1282, 1585, 1654,
1
2840, 3091. H NMR spectrum (400 MHz, CDCl ), δ,
2
4
3
reduced pressure. No purification was required.
ppm: 3.91 s (6H), 5.34 s (2H), 6.86 s (2H), 7.34 d (1H,
J = 15.560), 7.45 t (1H, J = 7.529), 7.53 t (2H, J =
General procedure for the synthesis of novel
E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-
β
7
1
8
.278), 7.65 d (2H, J = 8.533), 7.72 d (1H (H ) J =
5.560), 7.73 d (2H, J = 7.529), 7.88 d(2H, J = 8.533),
.16 s (1H). C NMR spectrum (DMSO, 100 MHz)
(
triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones (6a–6l).
The synthesis was performed in two steps. In the first
step, propargylated chalcones were synthesized from
propargyl bromide, DMF, and K CO . In the second
1
3
δC, ppm: 56.2, 65.1, 106.5, 120.4, 122.3, 127.4, 128.0,
29.6, 130.2, 131.3, 136.1, 138.4, 144.4, 153.2, 188.3.
M 520.
(E)-1-(4-Bromophenyl)-3-(3,5-dimethoxy)-4-[1-
(4-nitrophenyl-1H-triazol-4-yl] (6b). Reaction time
1
2
3
step, the propargylated chalcones were dissolved in
DMF, a pinch of CuSO , an aqueous solution of
4
sodium ascorbate, and different substituted azides 5a–
h were introduced into a solution. The reaction
–
1
5
57 h, yield 76%, mp 179–184°C. IR spectrum, ν, cm :
1
mixtures were kept stirring about 48–70 h to syn-
thesize 1,2,3-triazoles using “click chemistry.” Com-
pletion of the reactions was monitored by TLC. The
compounds were purified by column chromato-graphy.
Yield of the products varied between 65–88%.
1120, 1280, 1585, 1656, 2841, 3093, H NMR
spectrum (400 MHz, CDCl ), δ, ppm: 3.92 s (6H), 5.34
3
s (2H), 6.87 s (2H), 7.35 d (1H, J = 15.811), 7.66 d
(2H, J = 7.529), 7.72 d (1H, J = 15.811), 7.88 d (2H,
J = 7.529), 7.99 d (2H, J = 8.031), 8.31 s (1H), 8.43 d
13
(
2H, J = 8.031). C NMR spectrum (DMSO, 100
(E)-1-(4-Bromophenyl)-3-[3,5-dimethoxy-4-(prop-
MHz), δ , ppm: 56.1, 64.9, 106.6, 120.5, 123.8, 125.0,
C
2
-yn-1-yloxy)phenyl]prop-2-en-1-one (4a). Reaction
1
130.5, 131.7, 136.5, 137.8, 140.9, 144.7, 145.0, 146.6,
time 2 h, yield 82%, mp 143–145°C. H NMR spec-
1
53.2, 188.2. M 565.
E)-1-(4-Bromophenyl)-3-(3,5-dimethoxy)-4-{[1-
2-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy]-
phenyl}prop-2-en-1-one (6c). Reaction time 67 h,
trum (400 MHz, CDCl ), δ, ppm: 2.45 t (1H, J =
3
2
(
8
8
.503), 3.92 s (6H), 4.79 d (2H, J = 2.503), 6.86 s
(
α
2H), 7.35 d (1H, J = 15.811, H ), 7.65 d (2H, J =
(
β
.031), 7.72 d (1H, J = 15.811, H ), 7.88 d (2H, J =
1
3
–
1
.031). C NMR spectrum (DMSO, 100 MHz), δC,
yield 75%, mp 172–176°C. IR spectrum, ν, cm :
1
1
ppm: 56.2, 57.0, 76.5, 78.3, 102.2, 120.0, 126.1, 129.3,
30.5, 132.4, 135.2, 138.1, 144.2, 153.6, 189.2. M 402.
E)-3-[3,5-Dimethoxy-4-(prop-2-yn-1-yloxy)phe-
120, 1280, 1585, 1656, 2841, 3093, H NMR spec-
1
trum (400 MHz, CDCl ), δ, ppm: 3.89 s (9H), 5.35 s
3
(
2H), 6.52–6.45 m (1H), 6.86 s (1H), 7.13–7.10 m
(
nyl]-1-(3-methoxyphenyl)prop-2-en-1-one (4b). Reac-
(4H), 7.39 m (3H), 7.56 d (1H, J = 18.823), 7.72 d
1
13
tion time 2 h, yield 82%, mp 155–159°C. H NMR
(2H, J = 18.823), 8.24 s (1H). C NMR spectrum
spectrum (400 MHz, CDCl ), δ, ppm: 2.45 t (1H, J =
(DMSO, 100 MHz), δ , ppm: 55.7, 56.0, 65.1, 106.6,
C
3
2
2
.259), 3.89 s (3H), 3.94 s (6H), 4.84 d (2H, J =
.259), 6.86 s (2H), 7.39 d (1H, J = 15.560), 7.43 d
112.9, 120.8, 120.9, 125.6, 126.2, 127.1, 130.4, 130.5,
130.6, 131.7, 136.6, 138.0, 143.1, 145.0, 151.5, 153.3,
188.2. M 550.
(
1H, J = 8.533), 7.54 q (1H), 7.59 d (1H, J = 8.533),
β
13
7
.72 d (1H, J = 15.560, H ). C NMR spectrum
(
E)-1-(4-Bromophenyl)-3-(3,5-dimethoxy-4-{[1-
(
DMSO, 100 MHz), δ , ppm: 55.6, 56.1, 57.2, 76.5,
C
(
p-tolyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-
7
1
8.1, 103.2, 114.5, 120.2, 121.0, 126.3, 130.5, 138.1,
52.5, 192.3. M 353.
2
1
-en-1-one (6d). Reaction time 65 h, yield 81%, mp
–1
50–153°C. IR spectrum, ν, cm : 1122, 1285, 1580,
1
(E)-1-(4-Bromophenyl)-3-(3,5-dimethoxy)-4-{[(1-
1655, 2842, 3091. H NMR spectrum (400 MHz,
phenyl-1H-triazol-4-yl)methoxy]phenyl}prop-2-en-
CDCl ), δ, ppm: 2.42 s (3H), 3.90 s (6H), 5.33 s (2H),
3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016

SYNTHESIS, CHARACTERIZATION, AND ANTIMICROBIAL ACTIVITY
1409
–
1
6
1
7
.85 s (2H), 7.32 d (J = 8.031), 7.33 d (1H, J =
5.811), 7.60 d (2H, J = 8.031), 7.65 d (2H, J = 8.282),
.71 d (1H, J = 15.811), 7.88 d (2H, J = 8.282), 8.11 s
yield 73%, mp 172–177°C. IR spectrum, ν, cm : 1125,
1
1281, 1580, 1655, 2843, 3092. H NMR spectrum
(400 MHz, CDCl ), δ, ppm: 3.93 s (9H), 5.38 s (2H),
3
13
(1H). C NMR spectrum (DMSO, 100 MHz), δ , ppm:
6.88 s (2H), 7.15 s (2H), 7.39 d (1H, J = 16.815), 7.61–
7.54 m (2H), 7.72 d (1H, J = 16.815), 7.98 d (2H, J =
C
2
1
1
1.3, 56.5, 62.4, 103.0, 116.2, 120.06, 126.2, 128.6,
29.0, 130.1, 132.3, 133.1, 134.4, 136.0, 138.4, 153.5,
88.0. M 534.
1
3
6.776), 8.29 s (1H), 8.43 d (2H, J = 6.776). C NMR
spectrum (DMSO, 100 MHz), δ , ppm: 55.3, 56.09,
6.17, 64.5, 106.6, 113.1, 118.8,121.0, 121.4, 123.1,
C
5
1
1
(E)-1-(4-Bromophenyl)-3-{4-[(1-(3-chlorophenyl)-
23.2, 125.5, 129.8, 130.6, 132.0, 137.7, 139.0, 140.7,
44.4, 144.8, 145.1, 146.7, 153.2, 159.5,191.5. M 516.
1H-1,2,3-triazol-4-yl)methoxy]-3,5-dimethoxyphenyl]-
prop-2-en-1-one (6e). Reaction time 55 h, yield 76%,
mp 159–162°C. IR spectrum, ν, cm : 1120, 1280,
–
1
(
E)-3-{4-[(1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-
yl)methoxy]-3,5-dimethoxyphenyl}-1-(3-methoxy-
phenyl)prop-2-en-1-one (6i). Reaction time 72 h,
yield 68%, mp 151–156°C 1123, 1284, 1583, 1655,
1
1
585, 1656, 2841, 3093. H NMR spectrum (400 MHz,
DMSO), δ, ppm: 3.84 s (6H), 5.12 s (2H), 7.26 s (2H),
.56 d (1H, J = 6.776), 7.64 t (1H, J = 7.780), 7.72 d
1H, J = 15.560), 7.80 d (2H, J = 7.780), 7.88 d (1H,
J = 15.560), 7.93 d (1H, J = 6.776), 8.11–8.07 m (3H),
7
(
1
2
842, 3095. H NMR spectrum (400 MHz, DMSO), δ,
ppm: 3.85 s (9H), 5.15 s (2H), 7.25 s (3H), 7.51 t (1H,
J = 7.780), 7.61 s (1H), 7.70 d (1H, J = 15.560), 7.79 d
(1H, J = 8.031), 7.88 d (1H, J = 15.560), 8.11 d (2H,
J = 7.780), 8.17 d (2H, J = 8.031), 9.00 s (1H).
NMR spectrum (DMSO, 100 MHz), δ , ppm: 55.3,
1
3
8
.94 s (1H). C NMR spectrum (DMSO, 100 MHz),
δC, ppm: 55.2, 56.3, 65.4, 106.5, 113.2, 118.4, 119.0,
1
3
1
1
21.1, 122.5, 128.3, 129.4, 130.1, 131.5, 134.3, 137.5,
39.2, 144.3, 153.6, 159.7, 188.8. M 554.
C
C
5
1
1
6.1, 65.0, 106, 113.5, 118.1, 119.5, 121.0, 121.4,
22.8, 128.4, 129.8, 130.6, 131.5, 134.2, 137.6, 139.8,
44.0, 153.4, 159.2, 188.5. M 505.
(
E)-3-{4-[(1-(4-Acetophenyl-1H-pyrazol-4-yl)-
methoxy)-3,5-dimethoxyphenyl]-1-(4-bromophenyl}-
prop-2-en-1-one (6f). Reaction time 65 h, yield 85%,
mp 157–160°C IR spectrum, ν, cm : 1120, 1283, 1584,
654, 2843, 3091. H NMR spectrum (400 MHz,
CDCl ), δ, ppm: 2.68 s (3H), 3.91 s (6H), 5.35 s (2H),
.86 s (2H), 7.35 d (1H, J = 16.062, H ), 7.65 d (2H,
J = 12.548, Ar-Hs) 7.72 d (1H, J = 16.062, H ), 7.88 d
2H, J = 8.031), 8.02 d (2H, J = 8.031), 8.19 s (1H),
.27 d (2H, J = 12.548). C NMR spectrum (DMSO,
00 MHz), δ , ppm: 27.1, 55.4, 56.6, 65.5, 107.1, 113.7,
19.5, 120.1, 121.5, 123.0, 128.5, 130.3, 131.5, 132.4,
36.1, 138.5, 139.4, 140.8, 145.6, 153.5, 159.0, 189.3,
97.1. M 562.
–1
(E)-3-{4-[(2,6-Dimethoxy-4-(3-(3-methoxyphenyl)-
1
1
3
-oxoprop-1-en-1-yl)phenoxy)methyl]-1H-1,2,3-tri-
3
azol-1-yl}benzoic acid (6j). Reaction time 66 h, yield
6
1
α
6
–1
5%, mp 160–164°C. IR spectrum, ν, cm : 1121,
β
1
283, 1586, 1657, 2842, 3092. H NMR spectrum (400
(
MHz, DMSO), δ, ppm: 3.82 s (9H), 5.13 s (2H), 7.25 s
4H), 7.51 t (1H, J = 7.278), 7.61 s (1H), 7.70 d (1H,
J = 15.560), 7.79 d (2H, J = 7.278), 7.88 d (1H, J =
13
8
1
1
1
1
(
C
13
1
5.560), 8.16 d (2H, J = 7.207), 8.97 s (1H). C NMR
spectrum (DMSO, 100 MHz), δ , ppm: 55.8, 56.6,
6
1
C
5.3, 107.0, 113.6, 119.4, 121.6, 121.9, 123.4, 124.5,
30.5, 131.1, 138.2, 139.5, 145.0, 153.7, 159.9, 189.4.
(
E)-3-{4-[(4-(3-(4-Bromophenyl)-3-oxoprop-1-en-
M 515.
1
-yl)-2,6-dimethoxyphenoxy)methyl]-1H-1,2,3-
triazol-1-yl}benzoic acid (6g). Reaction time 68 h,
yield 72%, mp 177–181°C. IR spectrum: ν, cm .
(
E)-4-{4-[(2,6-Dimethoxy-4-(3-(3-methoxyphenyl)-
–
1
3
-oxoprop-1-en-1-yl)phenoxy)methyl]-1H-1,2,3-tri-
azol-1-yl}benzoic acid (6k). Reaction time 64 h, yield
7%, mp 168–172°C IR spectrum, ν, cm : 1122,
283, 1586, 1657, 2840, 3091. H NMR spectrum
400 MHz, CDCl ), δ, ppm: 3.84 s (9H), 5.13 s (2H),
.25 s (2H), 7.51 t (1H, J = 6.023), 7.61 s (2H), 7.70 d
1H, J = 16.816), 7.77 d (2H, J = 6.023), 7.87 d (1H,
J = 16.816), 8.16–8.06 m (3H), 8.95 s (1H). C NMR
1
1
123, 1284, 1586, 1657, 2844, 3092. H NMR spec-
trum (400 MHz, DMSO), δ, ppm: 3.84 s (6H), 5.12 s
2H), 7.25 s (2H), 7.72 d (1H, J = 15.309), 7.80 d (4H,
J = 8.031), 7.88 d (1H, J = 15.309), 8.10 d (4H, J =
–1
7
1
(
7
(
(
1
1
3
3
8
1
1
1
.031), 8.94 s (1H). C NMR spectrum (DMSO,
00 MHz), δ , ppm: 56.1, 65.8, 107.6, 119.5, 121.5,
24, 127.1, 130.2, 132.4, 137.6, 138.0, 140.8, 145.2,
C
13
53.5, 167.4, 188.3. M 564.
spectrum (DMSO, 100 MHz), δ , ppm: 55.7, 56.6,
C
(
E)-3-{3,5-Dimethoxy-4-[(1-(4-nitrophenyl)-1H-
107.0, 65.4, 107.0, 113.6, 119.3, 120.5, 121.5, 123.2,
129.1, 130.3, 131.1, 138.2, 139.5, 145.0, 153.7, 159.9,
189.3. M 515.
1
,2,3-triazol-4-yl)methoxy]phenyl}-1-(3-methoxy-
phenyl)prop-2-en-1-one (6h). Reaction time 70 h,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016

1
410
SUBHASHINI et al.
(
E)-3-{4-[(1-(4-Acetylphenyl)-1H-1,2,3-triazol-4-
phenyl}prop-2-en-1-ones, were synthesized in 65–88%
yield from substituted acetophenones, 4-hydroxy-3,5-
dimethoxybenzaldehyde, and different substituted
azides by the click chemistry method. All compounds
were screened for antibacterial activity against gram-
negative and gram-positive bacteria. Among them, the
excellent activity against gram-negative bacteria was
exhibited by compounds 6d and good activity, by the
compounds 6i, 6j, and 6f. The highest antibacterial
activity against gram-positive bacteria show com-
pounds 6d and 6i; the activity of the remaining com-
pounds is from poor to good. All compounds 6a–6l
were evaluated for antifungal activity against Sclerotium
rolfsii and Macrophomina phaseolina. It was shown
that at the concentration 5 mg/mL the compounds
show little activity.
yl)methoxy]-3,5-dimethoxyphenyl}-1-(3-methoxy-
phenyl)prop-2-en-1-one (6l). Reaction time 60 h,
yield 79%, mp 153–158°C. IR spectrum: ν, cm : 1122,
281, 1584, 1654, 2843, 3092. H NMR spectrum
–1
1
1
(
7
7
1
1
400 MHz, DMSO), δ, ppm: 3.84 s (9H), 5.12 s (2H),
.25 s (2H), 7.51 t (1H, J = 8.784), 7.54 d (2H, J =
.027), 7.63 d (2H, J = 8.784), 7.70 d (1H, Ar-H, J =
5.560), 7.79 d (1H, J = 7.027), 7.88 d (1H, J =
5.560), 7.94 d (1H, J = 7.278), 8.07 s (1H, Ar-H) 8.94
13
s (1H). C NMR spectrum (DMSO, 100 MHz), δ , ppm:
C
2
1
1
1
7.2, 55.8, 56.6, 65.4, 107.0, 113.2, 113.6, 119.0, 119.2,
20.2, 121.5, 121.9, 123.2, 128.9, 130.3, 130.5, 131.1,
32.1, 136.8, 138.2, 139.5, 140.0, 145.0, 153.3, 159.7,
89.9, 197.4. M 513.
Antimicrobial activity. The antimicrobial activity
was determined by the disk diffusion method in
nutrient agar, the zone of inhibition was measured in
mm. Nutrient agar medium was prepared from nutrient
broth (1.3 g, 100 mL) and agar agar (2%). The mixture
was autoclaved under the pressure 15 psi for 15 min.
The nutrient agar was poured into autoclaved petri
plates in a laminar flow cabinet. After the agar was
solidified, the bacterial culture (which was previously
inoculated in a nutrient broth and incubated at 37°C for
ACKNOWLEDGMENTS
The authors are thankful to The Head of the
Department of Chemistry at the Osmania University,
Hyderabad, for laboratory facilities and to the
Central Facilities for Research and Development at
the Osmania University, Hyderabad, for providing
analytical data. The study was supported in part by the
OU-DST-PURSE program (project A-37/PURSE/
coord/2014) and the University Grant Commission,
New Delhi.
2
4 h) was spread onto the plate by the spread plate
method. The compounds were introduced through the
wells made in the plate after spreading.
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