DONG ET AL.
5
0
(
(
(
C═O), 158.4 (C
4
), 154.5 (Pyrazole C
3
), 136.2 (C
1
), 134.4 (C
1
), 131.9
), 66.2
,C ),
); Mass: 444.39 (M + H)+; Elemental
: Calculated: C, 62.31; H, 6.14; N, 6.32; O,
.22. Found: C, 62.37; H, 6.18; N, 6.31; O, 7.19.
2.1.19
|
1-(5-(4-Hydroxyphenyl)-3-(4-nitrophenyl)-
0
0
0
0
0
C
3
,C
5
), 128.6 (C
2
,C
6
), 127.2 (C
2
,C
6
), 125.2 (C
4
), 115.9 (C ,C
3
5
4,5-dihydro-1H-pyrazol-1-yl)-2-propylpentan-
1-one (7 g)
Pyrazole C
0.5 (Aliphatic C
analysis for C23
5
), 45.2 (CH), 39.7 (Pyrazole C
,C ), 15.2 (CH
27BrN
4
), 35.3 (Aliphatic C
1
3
2
2
4
3
ꢂ
ꢀ1
H
2
O
2
Yield: 81%; M.p: 264–265 C; MW: 409.49; R
f
: 0.59; FTIR (Vmax; cm
7
KBr): 3269.21 (O H stretching), 3028.36 (Aromatic C H stretching),
963.87 (CH stretching), 2935.18 (CH stretching), 2862.83 (CH
stretching), 1714.08 (C═O stretching), 1675.32 (C═N stretching),
2
3
2
3
2
4
1
.1.17
|
1-(5-(4-Hydroxyphenyl)-3-(p-tolyl)-
1537.52 (NO
2
stretching), 1527.62 (C═C stretching), 1389.76 (N
N
1
,5-dihydro-1H-pyrazol-1-yl)-2-propylpentan-
-one (7e)
stretching), 742.18; H NMR (400 MHz, DMSO-d6, TMS) δ ppm: 9.26
(s, 1H, Ar OH), 8.10 (d, 2H, J = 7.87 Hz,Ar H), 7.61 (d, 2H,
J = 1.92 Hz, Ar H), 7.22 (d, 2H, J = 1.28 Hz, Ar H), 6.64 (d, 2H,
J = 2.08 Hz, Ar H), 5.78 (d, 1H, J = 4.29 Hz, pyrazole-H), 3.23 (d, 2H,
J = 8.07 Hz, pyrazole-H), 2.38 (q, 1H, J = 7.56 Hz, CH), 1.50–0.87 (m,
ꢂ
ꢀ1
Yield: 68%; M.p: 241–242 C; MW: 378.52; R
f
: 0.51; FTIR (Vmax; cm
KBr): 3269.23 (O H stretching), 3025.47 (Aromatic C H stretching),
961.87 (CH3 stretching), 2938.12 (CH stretching), 2863.82 (CH
13
2
2
3
14H, aliphatic-H);
(C═O), 158.6 (C ), 152.3 (Pyrazole C
(C ), 128.1 (C ,C
(Pyrazole C
20.6 (Aliphatic C
analysis for C23
15.63. Found: C, 67.51; H, 6.65; N, 10.29; O, 15.61.
C NMR (100 MHz, DMSO-d6) δ ppm:179.1
0
0
stretching), 1715.04 (C═O stretching), 1675.32 (C═N stretching),
4
3
), 150.2 (C
4
), 142.7 (C
1
), 134.5
,C ), 66.8
,C ),
); Mass: 410.50 (M + H)+; Elemental
: Calculated: C, 67.46; H, 6.65; N, 10.26; O,
1
0
0
0
0
1
523.61 (C═C stretching), 1388.79 (N N stretching), 743.15;
H
1
2
6
), 127.9 (C
2
,C
6
), 127.1 (C
3
,C
5
), 115.9 (C
3
5
NMR (400 MHz, DMSO-d6, TMS) δ ppm: 9.12 (s, 1H, Ar OH), 7.49
d, 2H, J = 7.34 Hz,Ar H), 7.21 (d, 2H, J = 1.04 Hz, Ar H), 7.13 (d,
H, J = 1.27 Hz, Ar H), 6.63 (d, 2H, J = 2.05 Hz, Ar H), 5.69 (d, 1H,
J = 4.29 Hz, pyrazole-H), 3.23 (d, 2H, J = 8.09 Hz, pyrazole-H), 2.42
q, 1H, J = 7.58 Hz, CH), 2.24 (s, 3H, CH3), 1.53–0.92 (m, 14H,
5
), 44.3 (CH), 39.8 (Pyrazole C
,C ), 14.2 (CH
4
), 35.5 (Aliphatic C
1
3
(
2
4
3
2
H
27 3
N O
4
(
13
aliphatic-H); C NMR (100 MHz, DMSO-d6) δ ppm:179.2 (C═O),
0
0
1
57.8 (C
4
), 152.1 (Pyrazole C
3
), 140.9 (C
4
), 134.6 (C
,C ), 115.8 (C
), 35.6 (Aliphatic C
); Mass: 379.51 (M + H)
: Calculated: C, 76.16; H,
.99; N, 7.40; O, 8.45. Found: C, 76.19; H, 8.02; N, 7.42; O, 8.46.
1
), 133.7 (C
,C ), 68.2
,C ),
1
),
2.1.20
|
1-(3,5-Bis(4-hydroxyphenyl)-4,5-dihydro-
0
0
0
0
1
29.1 (C
3
. C
5
), 127.9 (C
2
,C
6
), 127.2 (C
2
6
3
5
1H-pyrazol-1-yl)-2-propylpentan-1-one (7 h)
(
Pyrazole C
1.4 (CH ), 20.5 (Aliphatic C
; Elemental analysis for C24
5
), 45.3 (CH), 39.8 (Pyrazole C
,C ), 14.3 (CH
4
1
3
ꢂ
ꢀ1
2
3
2
4
3
Yield: 68%; M.p: 272–273 C; MW: 380.49; R
f
: 0.62; FTIR (Vmax; cm
+
30 2
H N O
2
KBr): 3273.23 (O H stretching), 3025.32 (Aromatic C H stretching),
2968.82 (CH stretching), 2939.17 (CH stretching), 2864.85 (CH
7
3
2
3
stretching), 1718.09 (C═O stretching), 1678.35 (C═N stretching),
1
1529.61 (C═C stretching), 1386.72 (N N stretching), 741.15;
H
2
3
2
.1.18
|
1-(5-(4-Hydroxyphenyl)-
NMR (400 MHz, DMSO-d6, TMS) δ ppm: 9.32 (s, 2H, Ar OH), 7.42
(d, 2H, J = 7.81 Hz, Ar H), 7.24 (d, 2H, J = 1.05 Hz, Ar H), 7.18 (d,
2H, J = 1.58 Hz, Ar H), 6.67 (d, 2H, J = 2.03 Hz, Ar H), 5.69 (d, 1H,
J = 4.21 Hz, pyrazole-H), 3.21 (d, 2H, J = 8.03 Hz, pyrazole-H), 2.42
-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-
-propylpentan-1-one (7f )
ꢂ
ꢀ1
13
Yield: 75%; M.p: 252–253 C; MW: 394.52; R
f
: 0.54; FTIR (Vmax; cm
(q, 1H, J = 7.59 Hz, CH), 1.54–0.91 (m, 14H, aliphatic-H); C NMR
0
KBr): 3265.29 (O H stretching), 3024.41 (Aromatic C H stretching),
967.82 (CH stretching), 2932.11 (CH stretching), 2868.84 (CH
stretching), 2832.47 (OCH stretching), 1718.09 (C═O stretching),
678.35 (C═N stretching), 1524.69 (C═C stretching), 1385.72 (N
(100 MHz, DMSO-d6) δ ppm:178.2 (C═O), 160.9 (C
4
), 157.5 (C
4
),
0
0
0
2
3
2
3
152.2 (Pyrazole C
3
), 134.5 (C
), 115.8 (C
), 35.4 (Aliphatic C
Mass: 381.48 (M + H)+; Elemental analysis for
1
), 129.1 (C
,C ), 66.7 (Pyrazole C
,C ), 20.4 (Aliphatic C
2
,C
6
), 128.9 (C
), 45.2 (CH), 39.8
,C ), 14.3 (CH );
1
), 127.1 (C
2
,
0
0
3
C
6
) 116.1 (C
3
,C
5
3
5
5
1
N
(Pyrazole C
4
1
3
2
4
3
1
stretching), 748.12; H NMR (400 MHz, DMSO-d6, TMS) δ ppm: 9.23
s, 1H, Ar OH), 7.45 (d, 2H, J = 7.82 Hz,Ar H), 7.28 (d, 2H,
23 28 2 3
C H N O :
(
Calculated: C, 72.60; H, 7.42; N, 7.36; O, 12.61. Found: C, 72.64; H,
7.40; N, 7.37; O, 12.58.
J = 1.08 Hz, Ar H), 7.23 (d, 2H, J = 1.05 Hz, Ar H), 6.69 (d, 2H,
J = 2.06 Hz, Ar H), 5.67 (d, 1H, J = 4.23 Hz, pyrazole-H), 3.14 (d, 2H,
J = 8.02 Hz, pyrazole-H), 3.82 (s, 3H, OCH3), 2.42 (q, 1H,
1
3
J = 7.58 Hz, CH), 1.52–0.89 (m, 14H, aliphatic-H);
C
NMR
2.1.21
activity
|
In vitro NF-ĸB transcription inhibitory
0
(
100 MHz, DMSO-d6) δ ppm:178.9 (C═O), 162.8 (C
4
), 158.6 (C ),
0
1
), 127.1 (C
4
0
0
1
52.8 (Pyrazole C
), 115.9 (C ,C
5.2 (CH), 39.7 (Pyrazole C
3
), 135.2 (C
1
), 128.9 (C
2
,C
6
), 127.8 (C
), 55.9 (OCH
), 21.1 (Aliphatic C
); Mass: 395.52 (M + H)+; Elemental analysis for
: Calculated: C, 73.07; H, 7.67; N, 7.10; O, 12.17.
2
,
0
0
C
6
3
5
), 114.8 (C
3
,C
5
), 67.8 (Pyrazole C
5
3
),
The NF-ĸB transcription inhibitory activity of compound 7c was per-
formed in RAW264.7 macrophages obtained from ATCC, USA. The
inhibitory activity was measured using an earlier reported procedure via
employing Dual-Luciferase Reporter Assay System (Promega) according
to the manufacturer's instructions [Srivastava, Awatade, et al., 2015].
4
4
), 35.7 (Aliphatic C
1
,C
3
2
,
4 3
C ), 14.8 (CH
C
H N
24 30 2
O
3
Found: C, 73.04; H, 7.79; N, 7.12; O, 12.19.