Chalcone-Benzotriazole Conjugates as New Potential Antimicrobial Agents
8
.13 (d, 1H, J=8.2 Hz, 3,4-(CH
Ph-CH), 7.47-7.27 (m, 4H, BT-4,5,6,7-H), 7.22 (d, 1H,
J=8.2 Hz, 3,4-(CH Ph-5-H), 7.14 (t, 2H, J=7.8 Hz,
Ph-3,5-H), 7.12 (s, 1H, 3,4-(CH Ph-2-H), 7.04 (d, 1H,
J=7.7 Hz, Ph-4-H), 6.80 (d, 2H, J=7.8 Hz, Ph-2,6-H),
.47 (s, 3H, 3,4-(CH Ph-4-CH ), 2.37 (s, 3H, 3,4-
); C NMR (151 MHz, CDCl ) δ:
3
)
2
Ph-6-H), 7.71 (s, 1H,
Sythesis of (Z)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-3-
(
4-(dimethylamino)phenyl)-1-(3,4-dimethylphenyl)-
prop-2-en-1-one (5l)
3 2
)
3
)
2
Compound 5l (0.315 g) was obtained as yellow
crystal according to general procedure described for 5a
starting from 4-(dimethylamino)benzaldehyde (0.164 g,
1.10 mmol) and compound 3c (0.291 g, 1.10 mmol).
Yield: 72.3%; m.p. 195-196 ℃; IR (KBr) ν: 3114,
3041 (aromatic C-H, =C-H), 2970 (aliphatic C-
2
3
)
2
3
13
(CH
3
)
2
Ph-3-CH
3
3
1
1
1
93.16, 145.84, 142.99, 141.39, 137.43, 134.08, 133.37,
32.76, 132.23, 131.39, 131.31, 130.32, 128.94, 128.4,
1
1
28.25, 126.12, 124.18, 120.22, 109.94, 21.38, 19.93;
H), 1631 (C=O), 1593 (C=C), 1383, 1349 cm ; H
+
HRMS (ESI) calcd for C23
found 354.1603.
H
19
N
3
O [M+H] , 354.1606;
NMR (600 MHz, CDCl ) δ: 8.14 (d, 1H, J=8.0 Hz,
3
3,4-(CH ) Ph-6-H), 7.64 (s, 1H, 4-N(CH ) Ph-CH), 7.44
3
2
3 2
-
2
(
7.3 (m, 4H, BT-4,5,6,7-H), 7.09 [s, 1H, 3,4-(CH
-H], 7.03 [d, 1H, J=7.6 Hz, 3,4-(CH Ph-5-H], 6.53
d, 2H, J=8.6 Hz, 4-N(CH Ph-2,6-H), 6.36 (d, 2H,
Ph-3,5-H), 2.92 (s, 6H, N(CH ),
Ph-4-CH ), 2.36 (s, 3H, 3,4-
); C NMR (151 MHz, CDCl ) δ:
3 2
) Ph-
Synthesis of (Z)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-
3,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-
one (5j)
3 2
)
(
3 2
)
J=8.7 Hz, 4-N(CH
3
)
2
3 2
)
Compound 5j (0.271 g) was obtained as white solid
2
.44 (s, 3H, 3,4-(CH
3
)
2
3
according to general procedure described for 5a starting
from 4-fluorobenzaldehyde (0.162 g, 1.30 mmol) and
compound 3c (0.344 g, 1.30 mmol). Yield: 56.2%; m.p.
13
(CH
3
)
2
Ph-3-CH
3
3
1
1
1
1
4
93.31, 152.33, 145.94, 145.20, 140.25, 136.53, 135.34,
33.71, 133.21, 132.91, 131.83, 127.94, 127.72, 125.99,
23.94, 120.07, 118.73, 111.83, 110.15, 39.92, 21.3+3,
9.74; HRMS (ESI) calcd for C25
19.1848; found 419.1850.
1
=
94-195 ℃; IR (KBr) ν: 3114, 3051 (aromatic C-H,
C-H), 2961 (aliphatic C-H), 1631 (C=O), 1595
24 4
H N O [M+H] ,
1 1
(
C=C), 1383, 1349 cm ; H NMR (600 MHz, CDCl
δ: 8.14 (d, 1H, J=8.2 Hz, 3,4-(CH Ph-6-H), 7.67 (s,
H, 4-FPh-CH), 7.46-7.39, 7.04 (m, 4H, BT-4,5,6,7-
H), 7.23 (d, 1H, J=8.1 Hz, 3,4-(CH Ph-5-H), 7.12 (s,
Ph-2-H), 6.84 (t, 2H, J=8.5 Hz, 4-FPh-
,6-H), 6.81-6.77 (m, 2H, 4-FPh-3,5-H), 2.47 (s, 3H,
,4-(CH Ph-4-CH ), 2.36 (s, 3H, 3,4-(CH Ph-3-CH );
C NMR (151 MHz, CDCl ) δ: 192.97, 164.22, 145.86,
3
)
3 2
)
1
Synthesis of (Z)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-
(
4-fluoro-2-(piperidin-1-yl)phenyl)-3-(4-hydroxy-3-
3 2
)
methoxyphenyl)prop-2-en-1-one (5m)
1
2
3
3 2
H, 3,4-(CH )
Compound 5m (0.170 g) was obtained as yellow
solid from procedure for the preparation of compound
5h. Yield: 25.7%; m.p. 204-206 ℃; IR (KBr) ν: 3427
(OH), 3132, 3056 (aromatic C-H, =C-H), 2942
2
3
)
2
3
3
)
2
3
1
3
3
1
1
41.62, 141.45, 137.45, 133.93, 133.27, 132.60, 132.45,
32.25, 128.38, 127.57, 126.11, 124.31, 120.32, 116.36,
(aliphatic C-H), 2862 (CH ), 1630 (C=O), 1593 (C=
1 1
1
16.21, 109.83, 21.37, 19.91; HRMS (ESI) calcd for
C), 1513, 1349, 749 cm ; H NMR (600 MHz, CDCl )
δ: 8.09 (d, J=8.2 Hz, 1H, 4-F-2-C H N-Ph-6-H), 7.71
3
+
C
23
H18FN
3
O [M+H] , 394.1332; found 394.1331.
5
10
(
s, 1H, 4-OH-3-OCH
BT-4,5,6,7-H), 6.77 (d, 1H, J=8.3 Hz, 4-F-2-C
Ph-5-H), 6.73-6.66 (m, 3H, 4-OH-3-OCH Ph-2,5,6-H),
Ph-3-OH), 5.60 (s, 1H, 4-F-
10N-Ph-3-H), 3.18 (s, 3H, OCH ), 3.01 (t, 4H,
10N-2,6-2H), 1.66 (m, 4H, C 10N-3,5-2H), 1.51 (m,
10N-4-H); C NMR (151 MHz, CDCl ) δ:
92.59, 165.58, 154.32, 149.39, 146.78, 145.65, 143.23,
33.67, 132.06, 131.99, 128.94, 128.03, 127.63, 124.22,
23.66, 119.86, 114.75, 110.61, 110.46, 108.39, 105.91,
3
Ph-CH), 7.44-7.35, 7.23 (m, 4H,
Synthesis of (Z)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-
5
H10N-
(3,4-dimethylphenyl)-3-(4-hydroxy-3-methoxyphenyl)-
3
prop-2-en-1-one (5k)
6
2
C
2
1
1
1
5
.13 (s, 1H, 4-OH-3-OCH
-C
3
Compound 5k (0.381 g) was obtained as yellow sol-
id according to general procedure described for 5a
starting from 4-hydroxy-3-methoxybenzaldehyde (0.198
g, 1.30 mmol) and compound 3c (0.345 g, 1.30 mmol).
Yield: 73.5%; m.p. 176-178 ℃; IR (KBr) ν: 3420
5
H
3
5
H
5
H
13
H, C
5
H
3
(
(
OH), 3097, 3021 (aromatic C-H, =C-H), 2967
aliphatic C-H), 1633 (C=O), 1595 (C=C), 1349
5.27, 53.78, 25.87, 23.99; HRMS (ESI) calcd for
1 1
+
cm ; H NMR (600 MHz, CDCl
.3 Hz, 3,4-(CH Ph-6-H), 7.65 (s, 1H, 4-OH-3-OCH
Ph-CH), 7.47-7.27 (m, 4H, BT-4,5,6,7-H), 7.12 (s, 1H,
,4-(CH Ph-2-H), 7.05 (d, 1H, J=7.7 Hz, 3,4-(CH
Ph-5-H), 6.75 (d, 1H, J=8.3 Hz, 4-OH-3-OCH Ph-5-H),
Ph-6-H), 5.64 (s,
Ph-2-H), 3.21 (s, 3H, OCH ), 2.46 (s,
Ph-4-CH ), 2.37 (s, 3H, 3,4-(CH Ph-3-
); C NMR (151 MHz, CDCl ) δ: 193.33, 149.48,
3
) δ: 8.13 (d, 1H, J=
C
27
H25FN
4
O
3
[M+H] , 495.1808; found 495.1811.
8
3
)
2
3
-
Synthesis of (Z)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-3-
(
1
3-ethoxy-4-hydroxyphenyl)-1-(4-fluoro-2-(piperidin-
-yl)phenyl)prop-2-en-1-one (5n)
3
3
)
2
3 2
) -
3
6
1
3
CH
.68 (d, 1H, J=8.3 Hz, 4-OH-3-OCH
H, 4-OH-3-OCH
H, 3,4-(CH
3
Compound 5n (0.280 g) was obtained as yellow sol-
3
3
id according to general procedure described for 5a
starting from 3-ethoxy-4-hydroxybenzaldehyde (0.230 g,
1.39 mmol) and compound 3b (0.374 g, 1.37 mmol).
Yield: 42.0%; m.p. 197-198 ℃; IR (KBr) ν: 3426
(OH), 3115, 3031 (aromatic C-H, =C-H), 2925,
2850 (aliphatic C-H), 1630 (C=O), 1594 (C=C),
3
)
2
3
3 2
)
13
3
3
1
1
1
1
4
46.66, 145.81, 144.17, 140.95, 136.98, 134.53, 133.54,
32.07, 130.19, 128.32, 128.15, 127.73, 126.11, 124.32,
23.38, 119.97, 114.65, 110.60, 110.17, 55.28, 21.3+5,
1
1
9.82; HRMS (ESI) calcd for C24
H
21
N
3
O
3
[M+H] ,
1455, 1383, 1349, 738 cm ; H NMR (600 MHz,
CDCl ) δ: 8.10 (d, 1H, J=8.2 Hz, 4-F-2-C 10N-Ph-6-
22.1481; found 422.1486.
3
5
H
Chin. J. Chem. 2017, XX, 1—7
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
5