1
02
M. S. ABDEL-MAKSOUD ET AL.
1
3
(
t, J ¼ 8.0 Hz, 2H, –CH
2
NHSO
2 3
); C NMR (75 MHz, CDCl ) d 158.0, N-(3-((4-(3-(3-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)pyridin-2-
1
1
1
57.2, 146.5, 142.4, 140.5, 139.2, 136.4, 134.7, 132.0, 130.7, 130.2, yl)amino)propyl)-4-methylbenzenesulfonamide (2n)
29.4, 129.2, 128.8, 128.3, 127.8, 127.7, 127.4, 125.0, 122.1, 121.7, White solid (33%); mp 158–60 C; H NMR (400 MHz, CD OD) d
19.6, 117.3, 116.8, 112.3, 105.5 (Ar-C), 43.0 (CH
ꢁ
1
3
2
), 41.6 (CH
2
); LC- 8.06 (s, 1H, Ar-H), 7.79 (d, J ¼ 5.5 Hz, 1H, Ar-H), 7.72 (d, J ¼ 8.3 Hz,
þ
MS(m/z) calculated for C32
H
27
N
5
O
3
S: 561.66, found: 562.0 (M þ 1) . 2H, Ar-H), 7.41–7.25 (m, 7H, Ar-H), 7.19 (t, J ¼ 7.9 Hz, 1H, Ar-H),
6
.83 (ddd, J ¼ 8.3 Hz, 2.3 Hz, 1.0 Hz, 1H, Ar-H), 6.71–6.61 (m, 2H, Ar-
H), 6.51 (dd, J ¼ 5.5, 1.5 Hz, 1H, Ar-H), 6.34 (s, 1H, Ar-H), 3.13 (t,
N-(3-((4-(3-(3-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)pyridin-2-
yl)amino)propyl) benzenesulfonamide (2j)
White solid (37%); mp 154–6 C; H NMR (400 MHz, CDCl ) d 7.92
J ¼ 6.7 Hz, 2H, NH–CH –), 2.89 (t, J ¼ 6.8 Hz, 2H,–CH NHSO ), 2.41
2
2
2
13
(s, 3H, CH ), 1.60 (p, J ¼ 6.7 Hz, 2H, CH CH CH );
C NMR
3
2
2
2
ꢁ
1
3
(100 MHz, CD OD) d 158.9, 157.6, 146.7, 143.1, 141.9, 140.9, 139.3,
3
(
7
1
s, 1H, Ar-H), 7.81–7.74 (m, 3H, Ar-H), 7.51 (d, J ¼ 7.2 Hz, 1H, Ar-H),
1
1
38.9, 137.4, 130.8, 129.8, 129.3, 128.5, 127.7, 126.6, 125.2, 121.2,
19.8, 116.8, 115.9, 110.9, 105.4 (Ar-C), 40.2 (CH ), 38.2 (CH ), 28.9
), 20.1 (CH ); LC-MS(m/z) calculated for C30 S: 539.20,
found: 540.0 (M þ 1) .
.44 (t, J ¼ 7.6 Hz, 2H, Ar-H), 7.26 (s, 5H, Ar-H), 7.14 (t, J ¼ 7.9 Hz,
H, Ar-H), 6.87 (d, J ¼ 7.88 Hz, 1H, Ar-H), 6.74 (s, 1H, Ar-H), 6.60 (d,
2
2
(CH
2
3
29 5 3
H N O
þ
J ¼ 7.4 Hz, 1H, Ar-H), 6.51 (d, J ¼ 5.3 Hz, 1H, Ar-H), 6.11(s, 1H, Ar-H),
4
–
.83 (brs, 1H, NH), 3.06 (brs, 2H, NH–CH –), 2.88 (d, J ¼ 5.8 Hz, 2H,
2
CH NHSO ), 1.53 (p, J ¼ 5.8 Hz, 2H, CH CH CH ); LC-MS(m/z) calcu-
2
2
2
2
2
þ
lated for C H N O S: 525.63, found: 526.0 (M þ 1) .
N-(3-((4-(3-(3-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)pyridin-2-
yl)amino)propyl)-4-(trifluoromethyl)benzenesulfonamide (2o)
2
9 27 5 3
ꢁ
1
White solid (39%); mp 150–2 C; H NMR (400 MHz, CD OD) d
3
4
-Bromo-N-(3-((4-(3-(3-hydroxyphenyl)-1-phenyl-1H-pyrazol-4-
yl)pyridin-2-yl)amino)propyl)benzenesulfonamide (2k)
Light yellow solid (42%); mp 184–6 C; H NMR (400 MHz, CD OD) d
3
8
.09–7.99 (m, 3H, Ar-H), 7.87 (d, J ¼ 8.3 Hz, 2H, Ar-H), 7.80 (d,
J ¼ 5.5 Hz, 1H, Ar-H), 7.41–7.34 (m, 3H, Ar-H), 7.34–7.25 (m, 2H, Ar-
H), 7.20 (t, J ¼ 7.9 Hz, 1H, Ar-H), 6.83 (ddd, J ¼ 8.3 Hz, 2.4 Hz, 0.9 Hz,
ꢁ
1
8
.06 (s, 1H, Ar-H), 7.79 (d, J ¼ 5.2 Hz, 1H, Ar-H), 7.80–7.67 (m, 4H, Ar-
1
H, Ar-H), 6.71–6.63 (m, 2H, Ar-H), 6.52 (dd, J ¼ 5.6 Hz, 1.5 Hz, 1H,
H), 7.37–7.34 (m, 3H, Ar-H), 7.29–7.27 (m, 2H, Ar-H), 7.19 (t,
J¼ 8.4 Hz, 1H, Ar-H), 6.84–6.81 (m, 1H, Ar-H), 6.68 (s, 1H, Ar-H), 6.66
Ar-H), 6.36 (d, J ¼ 6.0 Hz, 1H, Ar-H), 3.16 (t, J ¼ 6.7 Hz, 2H,
NH–CH NHSO ), 1.64 (p, J ¼ 6.7 Hz,
2
–), 2.96 (t, J ¼ 6.8 Hz, 2H, –CH
2
2
1
3
(
s, 1H, Ar-H), 6.51 (dd, J ¼ 5.6 Hz, J ¼ 1.2 Hz, 1H, Ar-H), 6.34 (s, 1H, Ar- 2H, CH CH CH ); C NMR (100 MHz, CD OD) d 158.8, 157.6, 146.5,
2
2
2
3
H), 3.14 (t, J ¼ 8.0 Hz, 2H, NH–CH
2
–), 2.93 (t, J¼ 8.0 Hz, 2H, 142.0, 140.9, 139.3, 138.8, 130.7, 129.7, 128.5, 127.7, 127.3, 125.9,
13
–
CH
2
NHSO
2
); 1.61 (d, J ¼ 6.0 Hz, 2H, CH
2 2 2
CH CH ); C NMR (100 MHz, 125.2, 121.2, 119.7, 116.8, 115.9, 110.9, 105.5, (Ar-H), 40.2 (CH2),
CD OD) d 158.9, 157.6, 146.6, 141.9, 140.9, 139.7, 139.3, 138.9, 132.0, 38.1 (CH ), 28.9 (CH ); LC-MS(m/z) calculated for C H F N O S:
3
2 2 30 26 3 5 3
þ
1
1
30.8, 129.8, 128.5, 128.3, 127.7, 126.6, 125.2, 121.2, 119.8, 116.8, 593.20 found: 594.0 (M þ 1) .
15.9, 110.9, 105.4 (Ar-C), 40.2 (CH
26BrN
2
), 38.1 (CH
2
), 28.8 (CH
2
); LC-MS(m/
þ
z) calculated for C29
H
5 3
O
S: 604.10, found: 605.0 (M þ 1) .
3-Fluoro-N-(3-((4-(3-(3-hydroxyphenyl)-1-phenyl-1H-pyrazol-4-
yl)pyridin-2-yl)amino) propyl) benzenesulfonamide (2p)
White solid (41%); mp 120–2 C; H NMR (400 MHz, CD
1
4
-Chloro-N-(3-((4-(3-(3-hydroxyphenyl)-1-phenyl-1H-pyrazol-4-
ꢁ
3
OD) d 8.05
yl)pyridin-2-yl)amino)propyl) benzenesulfonamide (2l)
(s, 1H, Ar-H), 7.79 (d, J ¼ 5.5 Hz, 1H, Ar-H), 7.67 (d, J ¼ 7.9 Hz, 1H,
ꢁ
1
White solid (52%); mp 166–8 C; H NMR (400 MHz, CD OD) d 8.06 Ar-H), 7.63–7.51 (m, 2H, Ar-H), 7.41–7.25 (m, 6H, Ar-H), 7.19 (t,
3
(
(
1
s, 1H, Ar-H), 7.87–7.75 (m, 3H, Ar-H), 7.60–7.46 (m, 2H, Ar-H), 7.36 J ¼ 7.9 Hz, 1H, Ar-H), 6.87–6.79 (m, 1H, Ar-H), 6.67 (t, J ¼ 4.2 Hz, 2H,
t, J ¼ 5.8 Hz, 3H, Ar-H), 7.32–7.26 (m, 2H, Ar-H), 7.19 (t, J ¼ 7.9 Hz, Ar-H), 6.50 (dd, J ¼ 5.5 Hz, 1.3 Hz, 1H, Ar-H), 6.36 (s, 1H, Ar-H), 3.15
H, Ar-H), 6.83 (ddd, J ¼ 8.3 Hz, 2.3 Hz, 0.8 Hz, 1H, Ar-H), 6.67 (t, (t, J ¼ 6.7 Hz, 2H, NH–CH –), 2.93 (t, J ¼ 6.8 Hz, 2H, –CH NHSO ) ,
2
2
2
13
J ¼ 5.0 Hz, 2H, Ar-H), 6.51 (dd, J ¼ 5.5 Hz, 1.4 Hz, 1H, Ar-H), 6.34 (s, 1.63 (p, J ¼ 6.7 Hz, 2H, CH CH CH ), C NMR (100 MHz, CD OD) d
2
2
2
3
1
–
(
H, Ar-H), 3.14 (t, J ¼ 6.6 Hz, 2H, NH–CH -), 2.93 (t, J ¼ 6.8 Hz, 2H, 163.7, 161.2, 158.8, 157.6, 146.5, 142.7, 141.9, 140.9, 139.3, 138.9,
2
13
CH NHSO ), 1.61 (p, J ¼ 6.7 Hz, 2H, CH CH CH );
C NMR 130.9, 130.8, 130.8, 129.8, 128.5, 127.7, 125.2, 122.5, 122.5, 121.2,
2
2
2
2
2
100 MHz, CD OD) d 158.9, 157.6, 146.7, 141.9, 140.9, 139.3, 139.2, 119.8, 119.1, 118.9, 116.8, 115.9, 113.7, 113.5, 110.9, 105.5 (Ar-C),
3
1
1
38.9, 138.3, 130.8, 129.8, 129.0, 128.5, 128.2, 127.7, 125.2, 121.2, 40.2 (CH ), 38.2 (CH ), 28.9 (CH ); LC-MS(m/z) calculated for
2 2 2
þ
19.8, 116.8, 115.9, 110.9, 105.4 (Ar-C), 40.2 (CH ), 38.1 (CH ), 28.8 C H FN O S: 543.17, found: 544.0 (M þ 1) .
2
2
29 26
5 3
(CH ); LC-MS(m/z) calculated for C H ClN O S: 560.7, found:
2 29 26 5 3
þ
5
61.0 (M þ 1) .
N-(3-((4-(3-(3-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)pyridin-2-
yl)amino)propyl) naphthalene-1-sulfonamide (2q)
ꢁ
1
4
-Fluoro-N-(3-((4-(3-(3-hydroxyphenyl)-1-phenyl-1H-pyrazol-4-
White solid (40%); mp 168–70 C; H NMR (400 MHz, CD
8.40 (s, 1H, Ar-H), 8.01 (s, 1H, Ar-H), 7.97 (d, J ¼ 8.4 Hz, 2H, Ar-H),
OD) d 8.06 7.92 (d, J ¼ 8.0 Hz, 1H, Ar-H), 7.81 (dd, J ¼ 8.8 Hz, 1.6 Hz, 1H, Ar-H),
3
OD) d
yl)pyridin-2-yl)amino)propyl)benzenesulfonamide (2m)
White solid (45%); mp 144–6 C; H NMR (400 MHz, CD
ꢁ
1
3
(
7
s, 1H, Ar-H), 7.98–7.86 (m, 2H, Ar-H), 7.80 (d, J ¼ 5.5 Hz, 1H, Ar-H), 7.73 (d, J ¼ 5.2 Hz, 1H, Ar-H), 7.65–7.57 (m, 2H, Ar-H), 7.36–7.25 (m,
.37 (d, J¼ 6.6 Hz, 3H, Ar-H), 7.33–7.24 (m, 4H, Ar-H), 7.20 (t, 5H, Ar-H), 7.13 (t, J ¼ 8.0 Hz, 1H, Ar-H), 6.79 (dd, J ¼ 8.4 Hz, 2.0 Hz,
J¼ 7.8 Hz, 1H, Ar-H), 6.83 (d, J ¼ 8.2Hz, 1H, Ar-H), 6.67 (d, J ¼ 8.4 Hz, 1H, Ar-H), 6.62 (s, 1H, Ar-H), 6.59 (d, J ¼ 6.4 Hz, 1H, Ar-H), 6.46 (d,
2
H, Ar-H), 6.51 (d, J ¼ 5.5 Hz, 1H, Ar-H), 6.35 (s, 1H, Ar-H), 3.15 (t, J ¼ 4.8 Hz, 1H, Ar-H), 6.27 (s, 1H, Ar-H), 3.11 (t, J ¼ 6.8 Hz, 2H), 2.94
1
3
J¼ 6.6 Hz, 2H, NH–CH
2
–), 2.92 (t, J ¼ 6.7 Hz, 2H, –CH
2
NHSO
2
), (t, J ¼ 6.8 Hz, 2H, Ar-H), 1.60 (t, J ¼ 6.8 Hz, 2H, Ar-H); C NMR
13
1
1
1
1
.74–1.53 (m, 2H, CH CH CH ); C NMR (100 MHz, CD OD) d 158.9, (100 MHz, CD OD) d 158.7, 157.6, 146.4, 141.9, 140.9, 139.3, 138.9,
57.6, 146.7, 141.9, 139.3, 138.8, 136.7, 130.8, 129.7, 129.5, 129.4, 137.2, 134.7, 132.1, 130.7, 129.7, 129.1, 128.8, 128.5, 128.3, 127.7,
28.5, 127.7, 125.2, 121.2, 119.8, 116.8, 115.9, 115.8, 115.6, 110.9, 127.6, 127.5, 127.2, 125.2, 122.0, 121.2, 119.7, 116.8, 115.9, 110.9,
2 2 2 3
3
05.4 (Ar-C), 40.2 (CH
2 2 2
2 2 2
), 38.2 (CH ), 28.8 (CH ); LC-MS(m/z) calculated 105.3 (Ar-C), 40.2 (CH ), 38.2 (CH ), 28.8 (CH ); LC-MS(m/z) calcu-
þ
þ
for C29
H26FN
5
O
3
S: 543.17, found: 544.0 (M þ 1) .
lated for C33
H
29
N
5 3
O
S: 575.20 found: 576.0 (M þ 1) .