Synthesis and Antimicrobial Activity of Bis-1,2,3-triazole Based Chalcones

Article abstract of DOI:10.1134/S1070363220010247

A series of bis-1,2,3-triazole based chalcones has been synthesized in high yields. The newly synthesized compounds are characterized by IR, NMR and mass spectroscopy. The combination of the pharmacologically active moieties in a single scaffold results i

Full text of DOI:10.1134/S1070363220010247

ISSN 1070-3632, Russian Journal of General Chemistry, 2020, Vol. 90, No. 1, pp. 154–159. © Pleiades Publishing, Ltd., 2020.
Synthesis and Antimicrobial Activity of Bis-1,2,3-triazole
Based Chalcones
V. Sunithaa,A. Kishore Kumara,b, P. Jalapathib,*, and Ch. Abraham Lincolnc
a Department of Chemistry, University College of Science, Osmania University, Saifabad, Hyderabad,
Telangana, 500004 India
b Department of Humanities and Sciences, Vardhaman College of Engineering, Shamshabad, Hyderabad,
Telangana, 501218 India
c Department of Chemistry, University College of Science, Osmania University, Hyderabad, Telangana, 500007 India
*e-mail: pochampalli.ou.chemi@gmail.com
Received December 13, 2019; revised January 20, 2020; accepted January 28, 2020
Abstract—A series of bis-1,2,3-triazole based chalcones has been synthesized in high yields. The newly synthe-
sized compounds are characterized by IR, NMR and mass spectroscopy. The combination of the pharmacologically
active moieties in a single scaffold results in their synergistic effect and high antimicrobial activity against several
bacterial and fungal strains. The compounds 4f, 4l, 4e, 4k, 4c, and 4i demonstrate potent antimicrobial activity at
concentrations of 75 and 100 μg/mL.
Keywords: bis-1,2,3-triazoles, chalcones, antimicrobial activity
DOI: 10.1134/S1070363220010247
In the current study we have reinforced biological
activities of 1,2,3-triazoles and chalcones by conjugating
these two pharmacophores in one molecular structure.
Such approach is a part of our ongoing research in syn-
thesis of biologically active compounds [1–3].
at concentrations of 75 and 100 μg/mL (Table 1). The
compounds 4b, 4h, 4a, and 4g also exhibited the pro-
nounced antibacterial activity against the tested bacterial
strains. The accumulated data indicated that presence of
the strong electron donating group (OMe) at ortho and
para positions of phenyl ring of chalcone could enhance
the antibacterial activity of the other products.
RESULTS AND DISCUSSION
Antifungal activity. According to the results obtained
(Table 2) the highest antifungal activity was determined
for compounds 4f, 4l, 4e, 4k, 4c, and 4i using Nystatin
as the standard drug.
Dialkylation of the substituted 1,3-dihydrobenzene
was carried out with propargyl bromide leading to the
corresponding derivative 2 with 98% yield (Scheme 1).
Its following click reaction with azides led to the cor-
responding ditriazole derivatives of acetophenone 3a,
3b in high yields. These intermediates were condensed
with a variety of substituted benzaldehydes under basic
conditions giving the target bis 1,3-triazolyl chalcones
4a–4l in high yields. The structures of the intermediates
and newly synthesized compounds 4a–4l were supported
by IR, NMR and mass spectral data.
EXPERIMENTAL
Commercially available reagents were used as sup-
plied, and all solvents were distilled before use. All
reactions were performed in an oven-dried glassware.
Melting points were measured in open capillary tubes
and are uncorrected. IR (KBr) spectra were recorded on
a Perkin–Elmer 337 spectrophotometer. NMR spectra
were measured on a Bruker AV-400 spectrometers using
DMSO-d6 as a solvent and TMS as the internal standard.
CHN analysis was carried out on a Perkin Elmer Model
2400 CHNS analyzer. ESI mass spectra were measured
on a QSTARXL hybrid MS system (Applied Bio Sys-
tems). TLC was carried out on Merck TLC silica gel 60
Antibacterial activity. The newly synthesized bis-
1,2,3-triazole based chalcones 4a–4l were tested for
their antibacterial activity. The compounds demonstrated
significant inhibition of tested gram positive and gram
negative strains compared to the standard drug Gen-
tamicin sulphate (Table 1). The compounds 4f, 4l, 4e,
4k, 4c, and 4i demonstrated high antibacterial activity
154

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF BIS-1,2,3-TRIAZOLE
155
Scheme 1. Synthesis of bis-1,2,3-triazole based chalcones 4a–4l.
Me
Br
O
O
O
R-N3
O
K2CO3, acetone
Reflux, 12 h, 98%
CuSO4·5H2O
Sodium ascorbate
DMF+H2O (1 : 1),
room temperature
HO
OH
1
2
O
N
N
N
N
N
N
N
N
N
N
R
N
N
R
R
H
R
R1
O
O
O
O
O
Ethanol, KOH
4 h,
room temperature
R1
4aꢂ4l
O
3aꢀꢁ3b
R =
Me
R = C6H12, R1 = H (4a), R = C6H12, R1 = 4-(Cl) (4b), R = C6H12, R1 = 2,4-(Cl) (4c), R = C6H12, R1 = 4-(CN) (4d);
R = C6H12, R1 = 4-(OMe) (4e), R = C6H12, R1 = 2,4-(OMe) (4f), R = C6H11, R1 = H (4g), R = C6H11, R1 = 4-(Cl) (4h);
R = C6H11, R1 = 2,4-(Cl) (4i), R = C6H11, R1 = 4-(CN) (4j), R = C6H11, R1 = 4-(OMe) (4k), R = C6H11, R1 = 2,4-(OMe) (4l).
F254 plates. The spots were visualized under UV light
at 254 nm or by staining with aqueous basic potassium
permanganate. Column chromatography was performed
on a Merck silica gel 60A (100–200 mesh).
17.22. C26H38N6O3. Calculated, %: C 64.71; H 7.94; N
17.41.
1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)me-
thoxy]phenyl}ethanone (3b). White solid, yield 92%,
mp 165–167°C. IR spectrum, ν, cm–1: 1675 (C=O). H
Synthesis of compounds 3a, 3b. To the solution
of 1-[2,4-bis(prop-2-yn-1-yloxy)phenyl]ethanone (2)
(100 mg, 0.438 mmol) in 5 mL of aqueous DMF (50%)
was added CuSO4·5H2O (5 mol %) followed by sodium
ascorbate (10 mol %) and alkyl azide (1.315 mmol). The
reaction mixture was stirred for 1 h at room temperature.
Upon completion of the process (TLC), the reaction
mixture was poured over crushed ice, the solid obtained
was filtered off, washed with water and dried. The crude
product was purified by column chromatography using
ethyl acetate in petroleum ether to afford the correspond-
ing 1,4-disubstituted 1,2,3-triazole derivative 3a, 3b.
1
NMR spectrum, δ, ppm: 8.37–8.20 m (2H), 7.67 d (J =
8.69 Hz, 1H), 7.02 s (1H), 6.73 d.d (J = 8.56 Hz, 2.4, 1H),
5.30 s (2H), 5.27 s (2H), 4.59–4.44 m (1H), 4.42–4.30 m
(1H), 2.60 s (3H), 2.06–1.12 m (20H). MS: m/z: 479
[M + H]+. Found, %: C 65.03; H 6.98; N 17.35.
C26H34N6O3. Calculated, %: C 65.25; H 7.16; N 17.56.
Synthesis of (E)-1-{2,4-bis[(1-hexyl-1H-1,2,3-
triazol-4-yl)methoxy]phenyl}-3-phenylprop-2-
en-1-one (4a). To a solution of compound 3a (1.0 g,
0.0043 mol) in EtOH was added KOH (0.370 g,
0.0065mol).Theresultingmixturewasstirredatroomtem-
perature for 15 min. Benzaldehyde (0.557 g, 0.0052 mol,
1.2eq)wasaddeddrop-wise, andthemixturewasstirredfor
8 h.After completion of the process (TLC), ice-cold water
was added to the reaction mixture and it was neutralized
by 0.1–0.2 N HCl, upon which precipitation occurred.
The precipitate was filtered off, washed with water and
cold MeOH to afford pure product 4a.
1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)methoxy]-
phenyl}ethanone (3a). White solid, yield 90%, mp
179–181°C. IR spectrum, ν, cm–1: 1674 (C=O). 1H NMR
spectrum, δ, ppm: 8.38–8.19 m (2H), 7.65 d (J = 8.68 Hz,
1H), 7.00 s (1H), 6.72 d.d (J = 8.54, 2.4 Hz, 1H), 5.31 s
(2H), 5.26 s (2H), 4.40–4.35 s (4H), 2.61 s (3H), 1.81 d
(J = 5.89 Hz, 4H), 1.24 s (12H), 0.83 d (J = 2.94 Hz, 6H).
MS: m/z: 483 [M + H]+. Found, %: C 64.50; H 7.72; N
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 1 2020

156
SUNITHA et al.
Table 1. Antibacterial activity of the compounds 4a–4l
Zone of inhibition, mm
gram negative bacteria
Bacillus Bacillus Pseudomonas Klebsiella Escherichia Proteus
gram positive bacteria
Compound c, μg/mL
Micrococcus
luteus
MRSA
subtilis cereus
aeruginosa
pneumonia
coli
24
26
26
28
29
30
22
24
29
32
32
35
22
25
25
27
27
29
15
17
28
31
31
34
31
33
vulgaris
20
23
22
24
26
28
19
20
28
31
31
34
19
21
21
23
24
26
14
16
27
30
30
33
29
31
4a
75
100
75
21
22
22
24
25
27
19
21
31
34
34
37
20
22
21
23
23
26
13
16
30
33
33
36
27
30
23
25
25
27
28
30
20
22
28
31
31
33
21
23
25
28
26
28
14
16
27
30
30
33
31
33
21
23
23
26
27
29
17
19
26
29
29
32
19
21
23
25
24
25
12
15
25
28
28
30
30
33
25
26
26
28
28
30
21
24
27
30
30
33
22
24
25
27
27
29
13
16
26
29
29
32
31
34
19
22
21
23
4b
21
23
100
75
24
25
4c
25
24
100
75
27
26
4d
17
19
100
75
19
21
4e
26
27
100
75
29
30
4f
29
30
100
75
32
33
4g
18
20
100
75
20
22
4h
20
22
100
75
23
24
4i
23
22
100
75
25
23
4j
11
12
100
75
14
15
4k
25
26
100
75
28
29
4l
28
29
100
75
31
32
Gentamicin
28
27
100
31
30
The compounds 4b–4l were synthesized according to
the above procedure using the appropriate benzaldehydes.
29.6, 29.5, 25.4, 25.3, 21.9, 21.8, 13.7. MS: m/z: 571
[M + H]+. Found, %: C 69.22; H 7.25; N 14.55.
C33H42N6O3. Calculated, %: C 69.45; H 7.42; N 14.73.
(E)-1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)me-
thoxy]phenyl}-3-phenylprop-2-en-1-one (4a). Yield
77%, white solid, mp 183–185°C. IR spectrum, ν, cm–1:
(E)-1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)me-
thoxy]phenyl}-3-(4-chlorophenyl)prop-2-en-1-one
(4b). White solid, yield 90%, mp 195–197°C. IR spec-
trum, ν, cm–1: 1658 (C=O). 1H NMR spectrum, δ, ppm:
8.31 s (1H), 8.20 s (1H), 7.76–7.35 m (7H), 7.12–6.97 m
(1H), 6.87–6.70 m (1H), 5.46–5.16 m (4H), 4.47–4.19 m
(4H), 1.33–1.06 m (12H), 1.88–1.58 m (4H), 0.92–0.75 m
(6H). 13C NMR spectrum, δC, ppm: 188.8, 162.9, 159.1,
143.3, 142.1, 140.5, 134.5, 131.8, 130.1, 128.7, 128.4,
1
1660 (C=O). H NMR spectrum, δ, ppm: 8.31 s (1H),
8.20 s (1H), 7.74–7.33 m (8H), 7.05 s (1H), 6.86–6.70 m
(1H), 5.47–5.15 m (4H), 4.51–4.14 m (4H), 1.93–1.55 m
(4H), 1.32–1.05 m (12H), 0.88–0.70 m (6H). 13C NMR
spectrum, δC, ppm: 188.5, 162.7, 159.0, 142.0, 142.0,
140.7, 134.8, 132.2, 130.0, 128.8, 128.2, 126.9, 124.6,
124.4, 121.4, 107.4, 100.1, 61.9, 61.4, 49.3, 30.5, 30.4,
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SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF BIS-1,2,3-TRIAZOLE
Table 2. Antifungal activity of the compounds 4a–4l
157
Zone of inhibition, mm
Compound c, μg/mL
Microsporum canis
Microsporum gypseum
Epidermophyton floccosum
4a
4b
75
100
75
7
5
5
10
8
9
13
12
11
100
75
15
15
13
4c
18
16
15
100
75
22
19
18
4d
No active
No active
No active
100
75
No active
No active
No active
4e
24
19
18
100
75
27
22
20
4f
26
22
21
100
75
28
25
24
4g
6
4
4
100
75
9
6
7
4h
13
12
11
100
75
16
15
14
4i
15
14
13
100
75
18
16
16
4j
No active
No active
No active
100
75
No active
No active
No active
4k
22
25
25
27
25
28
18
20
20
23
20
24
17
19
19
21
20
23
100
75
4l
100
75
Nystatin
100
127.7, 126.5, 124.5, 121.7, 107.5, 100.2, 61.8, 61.5, 49.5,
49.3, 30.7, 30.5, 29.7, 29.5, 25.6, 25.1, 21.9, 21.7, 13.7.
MS: m/z: 605 [M + H]+. Found: C 65.27; H 6.66; N 13.68.
C33H41ClN6O3. Calculated, %: C 65.49; H 6.83; N 13.89.
61.9, 61.7, 49.7, 49.6, 30.8, 30.6, 29.9, 29.7, 25.7, 25.5,
21.9, 21.7, 13.8. MS: m/z: 639 [M + H]+. Found, %: C
61.75; H 6.11; N 12.98. C33H40Cl2N6O3. Calculated, %:
C 61.97; H 6.30; N 13.14.
(E)-4-(3-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-oxoprop-1-en-1-yl)benzonitrile
(4d). White solid, yield 90%, mp 172–174°C. IR spec-
trum, ν, cm–1: 1660 (C=O). 1H NMR spectrum, δ, ppm:
8.30 s (1H), 8.20 s (1H), 7.77–7.37 m (7H), 7.15–6.98 m
(1H), 6.88–6.72 m (1H), 5.46–5.19 m (4H), 4.48–4.21 m
(4H), 1.35–1.07 m (12H), 1.89–1.58 m (4H), 0.91–0.76 m
(6H). 13C NMR spectrum, δC, ppm: 188.7, 162.8, 159.3,
143.3, 142.5, 140.7, 139.5, 132.8, 130.1, 128.7, 127.7,
126.5, 124.5, 119.2, 111.9, 107.8, 100.2, 61.7, 61.5, 49.6,
(E)-1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)me-
thoxy]phenyl}-3-(2,4-dichlorophenyl)prop-2-en-1-one
(4c). White solid, yield 90%, mp 221–223°C. IR spec-
trum, ν, cm–1: 1652 (C=O). 1H NMR spectrum, δ, ppm:
8.31–8.22 m (2H), 7.71 s (5H), 7.51–7.34 m (1H), 7.06 s
(1H), 6.92–6.70 m (1H), 5.48–5.16 m (4H), 4.49–4.17 m
(4H), 1.89–1.58 m (4H), 1.31–1.03 m (12H), 0.90–0.72 m
(6H). 13C NMR spectrum, δC, ppm: 188.6, 162.7, 159.4,
143.5, 142.4, 140.6, 136.2, 134.7, 132.0, 130.7, 130.3,
128.9, 128.5, 127.8, 126.7, 124.9, 121.5, 107.7, 100.4,
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SUNITHA et al.
(4h). White solid, yield 95%, mp 211–213°C. IR spec-
trum, ν, cm–1: 1656 (C=O). 1H NMR spectrum, δ, ppm:
8.32 s (1H), 8.21 s (1H), 7.78–7.36 m (7H), 7.14–6.97 m
(1H), 6.88–6.71 m (1H), 5.32 s (2H), 5.29 s (2H), 4.56–
4.42 m (1H), 4.44–4.32 m (1H), 2.08–1.14 m (20H). 13C
NMR spectrum, δC, ppm: 188.7, 162.8, 159.3, 143.5,
142.0, 140.7, 134.6, 131.6, 130.3, 128.6, 128.5, 127.7,
126.4, 124.6, 121.8, 107.5, 100.1, 62.6, 62.2, 60.3, 60.1,
33.5, 33.3, 33.1, 25.5, 25.3, 25.1, 25.0, 24.8. MS: m/z:
601 [M + H]+. Found, %: C 65.71; H 6.01; N 13.77.
C33H37ClN6O3. Calculated, %: C 65.93; H 6.20; N 13.98.
49.4, 30.8, 30.6, 29.7, 29.5, 25.6, 25.4, 21.8, 21.6, 13.9.
MS: m/z: 596 [M + H]+. Found, %: C 68.32; H 6.77; N
16.23. C34H41N7O3. Calculated, %: C 68.55; H 6.94; N 16.46.
(E)-1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(4-methoxyphenyl)prop-2-en-1-
one (4e). Light yellow amorphous solid, yield 95%, mp
161–163°C. IR spectrum, ν, cm–1: 1655 (C=O). 1H NMR
spectrum, δ, ppm: 8.31 s (1H), 8.20 s (1H), 7.76–7.35 m
(7H), 7.12–6.97 m (1H), 6.87–6.70 m (1H), 5.46–5.16 m
(4H), 4.47–4.19 m (4H), 3.82 (3H), 1.33–1.06 m (12H),
1.88–1.58 m (4H), 0.92–0.75 m (6H). 13C NMR spec-
trum, δC, ppm: 188.8, 162.9, 159.1, 155.6, 143.3, 142.1,
140.5, 131.8, 130.3, 129.1, 128.7, 127.7, 126.5, 115.2,
107.4, 100.1, 61.7, 61.5, 55.7, 49.6, 49.4, 30.6, 30.4,
29.7, 29.5, 25.6, 25.4, 21.9, 21.7, 13.8. MS: m/z: 601
[M + H]+. Found, %: C 67.77; H 7.17; N 13.76.
C34H44N6O4. Calculated, %: C 67.98; H 7.38; N 13.99.
(E)-1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(2,4-dichlorophenyl)prop-2-en-
1-one (4i). White solid, yield 88%, mp 237–239°C. IR
1
spectrum, ν, cm–1: 1650 (C=O). H NMR spectrum,
δ, ppm: 8.32 s (1H), 8.21 s (1H), 7.74–7.32 m (6H),
7.11–6.95 m (1H), 6.86–6.70 m (1H), 5.31 s (2H), 5.20 s
(2H), 4.57–4.43 m (1H), 4.45–4.33 m (1H), 2.06–1.15 m
(20H). 13C NMR spectrum, δC, ppm: 188.8, 162.8, 159.3,
143.6, 142.5, 140.5, 136.3, 134.6, 132.1, 130.7, 130.3,
128.8, 128.6, 127.7, 126.7, 124.6, 121.5, 107.6, 100.3,
62.8, 62.3, 60.5, 60.2, 33.5, 33.4, 33.2, 33.1, 25.3, 25.1,
25.0, 24.7. MS: m/z: 635 [M + H]+. Found, %: C 62.14;
H 5.49; N 13.03. C33H36Cl2N6O3. Calculated, %: C 62.36;
H 5.71; N 13.22.
(E)-1-{2,4-Bis[(1-hexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(furan-2-yl)prop-2-en-1-one (4f).
Light yellow amorphous solid, yield 88%, mp 143–145°C.
IR spectrum, ν, cm–1: 1654 (C=O). 1H NMR spectrum,
δ, ppm: 8.30 s (1H), 8.20 s (1H), 7.82 d (J = 16 Hz, 1H),
7.70–7.38 m (2H), 7.35 d (J = 16 Hz, 1H), 7.12–6.97 m
(1H), 6.87–6.70 m (1H), 6.49 d.d (J= 8.4, 2.4 Hz, 1H), 6.43
d (J = 2.4 Hz, 1H), 5.46–5.16 m (4H), 4.47–4.19 m (4H),
3.84 (3H), 3.82 (3H), 1.32–1.04 m (12H), 1.87–1.56 m
(4H), 0.93–0.75 m (6H). 13C NMR spectrum, δC, ppm:
189.0, 163.4, 163.0, 159.1, 156.5, 155.7, 143.4, 142.2,
140.6, 131.9, 130.2, 129.2, 128.9, 127.7, 126.5, 115.4,
107.6, 100.2, 61.6, 61.4, 55.7, 55.5, 49.5, 49.3, 30.6, 30.3,
29.7, 29.4, 25.6, 25.4, 21.9, 21.7, 13.7. MS: m/z: 631
[M + H]+. Found, %: C 66.40; H 7.12; N 13.11.
C35H46N6O5. Calculated, %: C 66.64; H 7.35; N 13.32.
(E)-4-(3-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-
4-yl)methoxy]phenyl}-3-oxoprop-1-en-1-yl)benzoni-
trile (4j). White solid, yield 96%, mp 184–186°C. IR
1
spectrum, ν, cm–1: 1658 (C=O). H NMR spectrum, δ,
ppm: 8.38 s (1H), 8.12 s (1H), 8.00–7.61 m (6H), 7.59–
7.46 s (1H), 7.07 s (1H), 6.91–6.72 s (1H), 5.45–5.17 m
(4H), 4.61–4.24 m (2H), 1.56 m (20H). 13C NMR spec-
trum, δC, ppm: 188.8, 162.6, 159.4, 143.5, 142.7, 140.5,
139.6, 132.9, 130.3, 128.5, 127.7, 126.4, 124.5, 119.3,
111.8, 107.8, 100.3, 62.7, 62.5, 60.4, 60.3, 33.5, 33.4,
33.1, 25.3, 25.1, 25.0, 24.6. MS: m/z: 592 [M + H]+.
Found, %: C 68.88; H 6.11; N 16.35. C34H37N7O3. Cal-
culated, %: C 69.02; H 6.30; N 16.57.
(E)-1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-phenylprop-2-en-1-one (4g). White
solid, yield 98%, mp 203–205°C. IR spectrum, ν, cm–1:
1655 (C=O). 1H NMR spectrum, δ, ppm: 8.37 s (1H), 8.15 s
(1H), 7.69–7.47 m (5H), 7.46–7.33 m (3H), 7.06 s (1H),
6.86–6.77 m (1H), 5.31 s (2H), 5.28 s (2H), 4.59–4.44 m
(1H), 4.42–4.30 m (1H), 2.06–1.12 m (20H). 13C NMR
spectrum, δC, ppm: 188.6, 162.9, 159.1, 142.4, 142.1,
140.2, 134.3, 133.1, 129.5, 128.6, 128.3, 126.8, 124.3,
124.1, 121.0, 107.3, 100.2, 62.7, 62.1, 60.2, 60.1, 33.5,
33.4, 33.2, 25.4, 25.2, 25.0, 24.9. MS: m/z: 567 [M +
H]+. Found, %: C 69.72; H 6.52; N 14.61. C33H38N6O3.
Calculated, %: C 69.94; H 6.76; N 14.83.
(E)-1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(4-methoxyphenyl)prop-2-en-
1-one (4k). Light yellow amorphous solid, yield 95%,
mp 179–181°C. IR spectrum, ν, cm–1: 1654 (C=O).
1H NMR spectrum, δ, ppm: 8.37 s (1H), 8.11 s (1H),
7.69–7.54 m (3H), 7.53–7.45 m (2H), 7.05 s (1H), 6.96 d
(J = 7.94 Hz, 2H), 6.80 d (J = 8.52 Hz, 1H), 5.36–5.22 m
(4H), 4.57–4.45 m (1H), 4.39–4.26 m (1H), 3.81 s (3H),
1.93–1.02 m (20H). 13C NMR spectrum, δC, ppm: 188.7,
162.8, 159.3, 155.8, 143.4, 142.0, 140.7, 131.6, 130.4,
(E)-1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(4-chlorophenyl)prop-2-en-1-one
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SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF BIS-1,2,3-TRIAZOLE
159
129.2, 128.8, 127.6, 126.4, 115.3, 107.5, 100.2, 62.7,
62.3, 60.3, 60.1, 33.5, 33.4, 33.2, 25.5, 25.4, 25.2, 25.0,
24.7. MS: m/z: 597 [M + H]+. Found, %: C 68.20; H
6.54; N 13.89. C34H40N6O4. Calculated, %: C 68.43; H
6.76; N 14.08.
5 mL of nutrient broth, and incubated at 37°C for 24 h
until a slight visible turbidity appeared. Turbidity of the
actively growing broth cultures was then adjusted with
broth to a density equivalent of a 0.5 McFarland standard,
and the resulting suspensions were used as the initial
inocula in the assay.
(E)-1-{2,4-Bis[(1-cyclohexyl-1H-1,2,3-triazol-4-yl)-
methoxy]phenyl}-3-(furan-2-yl)prop-2-en-1-one (4l).
Light yellow amorphous solid, yield 92%, mp 151–153°C.
IR spectrum, ν, cm–1: 1656 (C=O). 1H NMR spectrum,
δ, ppm: 8.29 s (1H), 8.20 s (1H), 7.80 d (J = 16 Hz, 1H),
7.72–7.40 m (2H), 7.35 d (J = 16 Hz, 1H), 7.12–6.97 m
(1H), 6.87–6.70 m (1H), 6.54–6.44 m (1H), 6.43 d
(J = 2.4 Hz, 1H), 5.36–5.22 m (4H), 4.56–4.46 m (1H),
4.40–4.27 m (1H), 3.81 s (3H), 3.79 s (3H), 1.95–1.03 m
(20H). 13C NMR spectrum, δC, ppm: 189.0, 163.4, 163.0,
159.1, 156.5, 155.7, 143.4, 142.2, 140.6, 131.9, 130.2,
129.2, 128.9, 127.7, 126.5, 115.4, 107.6, 100.2, 62.8,
62.5, 60.2, 60.0, 55.7, 55.5, 33.6, 33.4, 33.1, 25.6, 25.4,
25.2, 25.0, 24.6. MS: m/z: 627 [M + H]+. Found, %: C
66.89; H 6.57; N 13.00. C33H42N6O5. Calculated, %: C
67.07; H 6.75; N 13.41.
Antimicrobial assay. The initial inocula of the test
organisms, 100 μL, were swabbed over the surface of the
agar media (20 mL) in Petri dishes and let to be absorbed
for 15 min. Solutions of the test compounds in DMSO
(100 μL; c 75 and 100 mg/mL) were then loaded into the
wells and incubated in the air at 37°C for 24 h. The inhi-
bition zone diameters were measured with a zone reader
(HiAntibiotic Zone Scale). The standard drug Gentamicin
was used as a positive control.
CONCLUSIONS
Bis-1,4-disubstituted 1,2,3-triazole based chalcones
have been synthesized in high yields and their structures
supported by conventional spectroscopic methods. The
products have been characterized by high antimicrobial
activity with the highest activity determined for com-
pounds 4f, 4l, 4e, 4k, 4c, and 4i.
Antimicrobial activity. Bacterial and fungal strains.
Gram-positive strains Micrococcus luteus (ATCC
10240), methicillin-resistant Staphylococcus aureus
(MRSA, NCTC 13616), Bacillus subtilis (ATCC 6633),
and Bacillus cereus (ATCC 14579), and Gram-negative
strains Pseudomonas aeruginosa (ATCC 27853), Kleb-
siella pneumoniae (ATCC 43816), Escherichia coli
(ATCC 8739), and Proteus vulgaris (ATCC 13315)
were purchased from the American Type Culture Col-
lection. Methicillin-resistant Staphylococcus aureus
was purchased from the Public Health England Culture
Collections. Fungal strains Microsporum canis (ATCC-
36299), Microsporum gypseum (ATCC-24102), Epi-
dermophyton floccosum (ATCC-15694) were collected
from department of biotechnology, Chaitanya postgradu-
ate college (autonomous), Kishanpura, Hanamkonda,
Warangal, Telangana, 506001 India.All microbial strains
were stored at ‒80°C and streaked on Luria‒Bertani (LB)
agar plates (Hi-media Laboratories, Mumbai, India) and
incubated at 37°C for 20–24 h. A few isolated colonies
were selected from each plate and suspended in 5 mL
of LB broth in a sterile culture vessel. The vessel was
plugged with cotton and incubated with gentle shaking
(140 rpm) at 37°C for 20 h.
ACKNOWLEDGMENTS
V. Sunitha thanks the Head of the Department, UCS, Osma-
nia University, Saifabad, Hyderabad and Central Facilities for
Research and Development, Osmania University, Hyderabad,
India for providing analytical support.
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
REFERENCES
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the Kirby–Bauer disk diffusion assay [4], four to five
well-isolated colonies of the same morphological type
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