Med Chem Res
CH and CH), 6.99 (2H, d, J = 16.8 Hz, CH and CH), 7.12
2H, s, ArH), 7.68–7.70 (2H, d, J = 8.4 Hz, ArH),
J = 11.8 Hz, CH and CH), 6.87–6.88 (4H, m, ArH), 7.12
1
(2H, s, ArH), 9.14 (2H, s, ArOH); C NMR (100 MHz,
3
(
0 0
7
1
1
1
.86–7.88 (2H, d, J = 8.4 Hz, ArH), 9.14 (1H, s, ArOH),
1
DMSO-d ): d 182.19 (C=O), 151.12 (C3 and C5 pyri),
6
Ar
3
0.25 (1H, s, ArOH); C NMR (100 MHz, DMSO-d ): d
146.35 (2 9 C OCH ), 145.78 (Cpyr=N), 144.82
Ar 3
0
(2 9 C OH), 141.12 (C1 pyri), 134.32 (2 9 ArC–CH),
Ar
6
82.81 (C=O), 154.61 (C NH2), 151.71 (2 9 C OCH ),
Ar
Ar
3
0
0
44.12 (2 9 C OH), 146.71 (Cpyr=N), 134.32 (2 9 ArC–
Ar
131.71 (C2
and C6 ), 128.97 (2 9 C1 ), 123.83
Ar Ar
Ar
0
0
0
0
and C6 pyri) 120.17
pyri
CH), 130.81 (C2 and C6 ), 128.91 (2 9 C1 ), 123.81
Ar
(2 9 ArCH=CH), 123.44 (C2
Ar
Ar
(
2 9 ArCH=CH), 120.11 (2 9 C6 ), 116.91 (2 9 C5 ),
Ar
(2 9 C6 ), 116.51 (2 9 C5 ), 112.24 (2 9 C1 ), 107.92
Ar Ar Ar
Ar
0
0
?
(Cpyr), 56.10 (2 9 OCH ); EIMS m/z = 469.4 [M] . Anal.
1
16.63 (C3
and C5 ), 112.21 (2 9 C1 ), 106.92
Ar
Ar
Ar
3
?
Cpyr), 56.12 (2 9 OCH ); EIMS m/z = 408.5 [M] . Anal.
(
Calcd. for C H N O : C, 69.07; H, 4.94; N, 8.95. Found:
27 23 3 5
3
Calcd. for C H N O : C, 69.55; H, 5.21; N, 8.69. Found:
28 25 3 5
C, 69.09; H, 4.92; N, 8.94.
,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(2-
hydroxyphenyl)methanone (3f) Light Brown (EtOH), mp
C, 69.57; H, 5.19; N, 8.70.
3
3
,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(4-
1
68–170 °C; yield 74 %; IR (KBr) vmax: 3402, 3398, 1752,
chlorophenyl)methanone (3c) Yellow solid (EtOH), mp
1
-1 1
1
557, 1347 cm . H NMR (400 MHz, DMSO-d ): d 3.81
60–162 °C; yield 78 %; IR (KBr) vmax: 3406, 1745, 1562,
6
-
1
337, 698 cm . H NMR (400 MHz, DMSO-d ): 3.83
1
(6H, s, OCH ), 6.59 (1H, s, CH=C), 6.74 (2H, d,
3
1
6
J = 11.8 Hz, CH and CH), 6.85 (2, d, J = 11.8 Hz, ArH),
(
6H, s, OCH ), 6.61 (1H, s, CH=C), 6.75 (2H, d,
3
6
.82–7.92 (9H, m, ArH), 7.14 (2H, s, ArH), 9.13 (1H, s,
1
J = 11.6 Hz, CH and CH), 6.91 (2H, d, J = 11.6 Hz, CH
3
ArOH), 10.88 (1H, s, ArOH), 11.76 (1H, s, ArOH);
C
and CH), 6.93-7.89 (10H, m, ArH), 9.14 (2H, s, OH), 9.89
1
3
NMR (100 MHz, DMSO-d ): d 165.21 (C=O), 161.12
(
1H, s, OH); C NMR (100 MHz, DMSO-d ): d 181.98
6
6
0
(C2 OH), 152.23 (2 9 C OCH ), 147.78 (Cpyr=N),
Ar
(
C=O), 147.51 (2 9 C OCH ), 144.02 (2 9 C OH),
3
Ar
3
Ar
Ar
0
1
47.11
(2 9 C OH),
Ar
136.71
0
(C4 Ar),
133.42
1
1
45.71 (Cpyr=N), 140.11 (C Cl), 134.32 (2 9 ArC–CH),
Ar
0
0
(2 9 ArCH=CH), 131.10 (C6 ), 128.99 (2 9 C1Ar),
Ar
31.71 (C2
and C6 ), 128.97 (2 9 C1 ), 123.83
Ar Ar
Ar
0
123.61 (2 9 ArCH=CH), 121.6 (C5 ), 119.9 (2 9 C6Ar),
Ar
(
2 9 ArCH=CH), 120.17 (2 9 C6 ), 116.51 (2 9 C5 ),
Ar
Ar
0
0
116.61 (2 9 C5 ), 112.21 (2 9 C2 ), 107.31 (Cpyr),
Ar Ar
1
16.53 (C3
and C5 ), 112.24 (2 9 C1 ), 107.92
Ar
Ar
Ar
?
6.31 (2 9 OCH ); EIMS m/z = 484.5 [M] . Anal. Calcd.
?
Cpyr), 56.10 (2 9 OCH ); EIMS m/z = 503.0 [M] ; Anal.
5
(
3
3
for C H N O : C, 69.41; H, 4.99; N, 5.78. Found: C,
28 24 3 6
Calcd. for C H ClN O : C, 66.87; H, 4.61; N, 5.57.
2
8
23
2 5
69.39; H, 4.96; N, 5.80 (Zhichang et al., 2012).
Found: C, 66.84; H, 4.63; N, 5.54 (Balaji et al., 2015).
3
,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(2-
3
,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(2-
thiophenyl)methanone (3g) Light yellow solid (EtOH),
mp 120–122 °C; yield 65 %; IR (KBr) vmax: 3396, 1735,
chlorophenyl)methanone (3d) Yellow solid (EtOH), mp
1
68–170 °C; yield 74 %; IR (KBr) vmax: 3412, 1751, 1569,
-1 1
1
-1 1
1563, 1337 cm . H NMR (400 MHz, DMSO-d
): d 3.83
6H, s, OCH ), 6.61 (1H, s, CH=C), 6.76 (2H, d,
6
329, 699 cm . H NMR (400 MHz, DMSO-d ): d 3.83
6
(
3
(
6H, s, OCH ), 6.61 (1H, s, CH=C), 6.76 (2H, d,
3
J = 12.8 Hz, CH and CH), 6.89 (2H, d, J = 12.8 Hz, CH
1
and CH), 6.92–7.88 (9H, m, ArH), 10.53 (2H, s, OH);
J = 12.1 Hz, CH and CH), 6.90 (2H, d, J = 12.1 Hz, CH
1
and CH), 6.94-8.17 (10H, m, ArH), 9.15 (2H, s, OH);
3
3
C
C
NMR (100 MHz, DMSO-d ): d 182.21 (C=O), 152.23
6
NMR (100 MHz, DMSO-d ): d 181.83 (C=O), 147.53
6
0
(2 9 C OCH ), 145.21 (C1 ), 147.11 (2 9 C OH),
Ar
3
Ar
Ar
(
2 9 C OCH ), 143.32 (2 9 C OH), 141.71 (Cpyr=N),
Ar 3 Ar
0
0
1
44.78 (Cpyr=N), 137.71 (C5 Ar), 135.11 (C3 Ar), 133.49
0
37.11 (C Cl), 136.01 (C4 Ar), 134.39 (2 9 ArC–CH),
Ar
1
1
0
(2 9 ArCH=CH), 128.98 (C4 ), 128.19 (2 9 C1Ar),
Ar
0
0
31.71 (C5 Ar), 129.41 (C3 ), 128.97 (2 9 C1 ), 127.11
Ar
Ar
1
23.69 (2 9 ArCH=CH), 120.91 (2 9 C6 ), 116.71
Ar
0
(
C5 Ar), 123.13 (2 9 ArCH=CH), 120.19 (2 9 C6Ar),
(2 9 C5 ), 112.21 (2 9 C2 ), 106.37 (Cpyr), 56.12
Ar Ar
1
5
16.21 (2 9 C5 ), 112.14 (2 9 C1 ), 107.92 (Cpyr),
Ar Ar
?
?
6.12 (2 9 OCH ); EIMS m/z = 503.0 [M] . Anal. Calcd.
(2 9 OCH
); EIMS m/z = 475.1 [M] . Anal. Calcd. for
3
3
C H N O S: C, 65.81; H, 4.65; N, 5.90. Found: C, 65.84;
26 22 2 5
for C H ClN O : C, 66.87; H, 4.61; N, 5.57. Found: C,
2 5
2
8
23
H, 4.65; N, 5.94 (Balaji et al., 2015).
6
6.85; H, 4.63; N, 5.55 (Balaji et al., 2015).
3
,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(4-
3,5-Bis(4-hydroxy-3-methoxystyryl)-1H-pyrazole-1-yl-(phe-
nyl)ethanone (3h) Yellow solid (EtOH), mp 138–140 °C;
yield 82 %; IR (KBr) vmax: 3401, 1751, 1565, 1338 cm .
pyridyl)methanone (3e) Yellow solid (EtOH), mp
-
1
1
2
1
04–106 °C (found), 105–106 °C (reported) (Sahu et al.,
1
012); yield 74 %; IR (KBr) vmax: 3401, 1753, 1567, 1543,
-
H NMR (400 MHz, DMSO-d ): d 3.66 (2H, s, CH ), 3.83
6
2
1 1
342 cm . H NMR (400 MHz, DMSO-d ): d 3.81 (6H, s,
(6H, s, OCH ), 6.61 (1H, s, CH=C), 6.76 (2H, d,
3
6
OCH ), 6.60 (1H, s, CH=C), 6.75 (2H, d, J = 11.8 Hz, CH
3
J = 11.8 Hz, CH and CH), 6.89 (2H, d, J = 11.8 Hz, CH
1
3
and CH), 6.82 (4H, d, J = 7.8 Hz, ArH), 6.87 (2H, d,
and CH), 6.94–7.81 (11H, m, ArH), 9.15 (2H, s, OH);
C
1
23