Med Chem Res
3.84 (s, 3H, OCH3); 13C NMR (100 MHz, DMSO-d6) d
(ppm): 191.3 (C=O), 159.8 (C8a), 159.5 (C5), 159.3 (Ar–C),
(E)-1-(5-Hydroxy-2H-chromen-6-yl)-3-(1-phenyl-3-(p-
tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one (5d)
0
0
152.6 (C3 ), 138.5 (Ar–C), 134.5 (Ar–C), 131.1 (C5 ), 129.3
(Cb), 128.5 (C7), 126.8 (Ca), 126.7 (Ar–C), 123.7 (Ar–C),
Pale yellow solid; m.p.: 150–151 °C; IR (KBr) (cm-1): 3125
(OH), 2921 (H–C=), 1633 (a,b-unsaturated C=O); H NMR
1
0
120.4 (C3), 119.3 (C4), 118.2 (Ar–C), 117.2 (C6), 116.5 (C4 ),
(400 MHz,DMSO-d6)d(ppm):13.86(s, 1H,OH), 9.45(s, 1H,
pyrazole ring-H), 8.04 (d, 1H, Ar–H), 7.92 (m, 3H, Ar–H), 7.78
(d, 1H, Hb, J = 15.30 Hz), 7.58 (m, 4H, Ar–H), 7.40 (m, 3H,
Ar–H), 6.69 (d, 1H, Ar–H), 6.48 (d, 1H, Ar–CH=C), 5.88 (m,
1H, Ar–C=CH), 4.92 (d, 2H, O–CH2), 2.40 (s, 3H, Ar–CH3);
13C NMR (100 MHz, DMSO-d6) d (ppm): 191.2 (C=O), 159.7
114.0 (C4a), 113.5 (Ar–C), 109.3 (C8), 107.2 (Ar–C), 65.5
(OCH2), 54.9 (OCH3); MS (m/z): 451 (M ? H)?; Elemental
analysis (C28H22N2O4); calcd. C, 74.65; H, 4.92; N, 6.22;
found C, 74.63; H, 4.93; N, 6.21 %.
(E)-3-(3-(4-Ethoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-1-
0
(C8a), 159.2 (C5), 152.5 (C3 ), 138.3 (Ar–C), 134.1 (Ar–C),
(5-hydroxy-2H-chromen-6-yl)prop-2-en-1-one (5g)
0
132.2 (Ar–C), 131.0 (C5 ), 129.2 (Cb), 127.9 (Ar–C), 127.7
Pale yellow solid; m.p.: 154–156 °C; IR (KBr) (cm-1): 3132
(OH), 2979 (H–C=), 1633 (a,b-unsaturated C=O). 1H NMR
(400 MHz, DMSO-d6) d (ppm): 13.86 (s, 1H, OH), 9.43 (s,
1H, pyrazole ring-H), 8.03 (d, 1H, Ar–H), 7.91 (t, 3H, Ar–H),
7.78 (d, 1H, Hb, J = 15.29 Hz), 7.59 (m, 4H, Ar–H), 7.42 (t,
1H, Ar–H), 7.12 (d, 2H, Ar–H), 6.69 (d, 1H, Ar–H), 6.46 (d,
1H, Ar–CH=C), 5.87 (m, 1H, Ar–C=CH), 4.92 (s, 2H, O–
CH2), 4.12(q, 2H, OCH2), 1.37 (t, 3H, OCH2CH3); 13C NMR
(100 MHz, DMSO-d6) d (ppm): 191.5 (C=O), 160.0 (C8a),
(C7), 127.1 (Ar–C), 126.8 (Ar–C), 125.6 (Ca), 120.2 (C3),
0
119.5 (C4), 118.2 (Ar–C), 117.5 (C6), 116.3 (C4 ), 113.4 (C4a),
109.1 (C8), 107.1 (Ar–C), 65.3 (OCH2), 30.1 (CH3); MS (m/z):
435 (M ? H)?; Elemental analysis (C28H22N2O3); calcd. C,
77.40; H, 5.10; N, 6.45; found C, 77.42; H, 5.11; N, 6.44 %.
(E)-1-(5-Hydroxy-2H-chromen-6-yl)-3-(3-(4-
hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one
(5e)
0
159.6 (C5), 158.9 (Ar–C), 152.8 (C3 ), 138.8 (Ar–C), 134.9
Pale yellow solid; m.p.: 209–211 °C; IR (KBr) (cm-1):
3310 (Ar–OH), 3127 (OH), 2922 (H–C=), 1632 (a,b-un-
0
(Ar–C), 131.3 (C5 ), 129.5 (Ar–C), 128.7 (Cb), 127.0 (C7),
126.9 (Ca), 123.9 (Ar–C), 120.5 (C3), 119.5 (C4), 118.4 (Ar–
1
0
C), 117.4 (C6), 116.7 (C4 ), 114.6 (Ar–C), 113.8 (C4a), 109.5
saturated C=O); H NMR (400 MHz, DMSO-d6) d (ppm):
13.88 (s, 1H, OH), 9.82 (s, 1H, Ar–OH), 9.42 (s, 1H,
pyrazole ring-H), 8.03 (d, 1H, Ar–H), 7.90 (t, 3H, Ar–H),
7.79 (d, 1H, Hb, J = 15.10 Hz), 7.59 (t, 2H, Ar–H), 7.49 (t,
2H, Ar–H), 7.41 (t, 1H, Ar–H), 6.94 (d, 2H, Ar–H), 6.68 (d,
1H, Ar–H), 6.47 (d, 1H, Ar–CH=C), 5.87 (m, 1H, Ar–
C=CH), 4.92 (d, 2H, O–CH2); 13C NMR (100 MHz,
DMSO-d6) d (ppm): 191.7 (C=O), 160.2 (C8a), 159.7 (C5),
(C8), 107.4 (Ar–C), 65.7 (C2-OCH2), 63.0 (OCH2), 14.5
(CH3); MS (m/z): 465 (M ? H)?; Elemental analysis
(C29H24N2O4); calcd. C, 74.98; H, 5.21; N, 6.03; found C,
74.96; H, 5.22; N, 6.01 %.
(E)-3-(3-(3-Ethoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-1-
(5-hydroxy-2H-chromen-6-yl)prop-2-en-1-one (5h)
0
0
158.1 (Ar–C), 153.3 (C3 ), 135.1 (Ar–C), 131.4 (C5 ), 129.7
(Cb), 127.5 (Ar–C), 127.1 (C7), 125.3 (Ca), 122.4 (Ar–C),
120.6 (C3), 119.4 (C4), 118.5 (Ar–C), 117.4 (C6), 116.9
Pale yellow solid; m.p.: 176–178 °C; IR (KBr) (cm-1):
3143 (OH), 2927 (H–C=), 1634 (a,b-unsaturated C=O); 1H
NMR (400 MHz, CDCl3) d (ppm): 13.69 (s, 1H, OH), 8.34
(s, 1H, pyrazole ring-H), 7.95 (d, 1H, Hb, J = 15.48 Hz),
7.79 (d, 2H, Ar–H), 7.52 (d, 3H, Ar–H), 7.39 (m, 3H, Ar–
H), 7.24 (q, 2H, Ar–H), 6.98 (m, 1H, Ar–H), 6.82 (d, 1H,
Ar–H), 6.32 (d, 1H, Ar–CH=C), 5.71 (m, 1H, Ar–C=CH),
4.90 (dd, 2H, O–CH2), 4.10 (q, 2H, OCH2), 1.49 (t, 3H,
OCH2CH3); 13C NMR (100 MHz, DMSO-d6) d (ppm):
191.6 (C=O), 160.6 (C8a), 160.4 (C5), 159.1 (Ar–C), 153.7
0
(C4 ), 115.6 (Ar–C), 114.2 (C4a), 113.8 (Ar–C), 109.6 (C8),
107.5 (Ar–C), 65.8 (OCH2); MS (m/z): 437 (M ? H)?;
Elemental analysis (C27H20N2O4); calcd. C, 74.30; H, 4.62;
N, 6.42; found C, 74.29; H, 4.63; N, 6.44 %.
(E)-1-(5-Hydroxy-2H-chromen-6-yl)-3-(3-(4-
methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-
one (5f)
0
(C3 ), 139.3 (Ar–C), 134.9 (Ar–C), 133.4 (Ar–C), 130.5
Pale yellow solid; m.p.: 168–170 °C; IR (KBr) (cm-1): 3129
(OH), 2977 (H–C=), 1634 (a,b-unsaturated C=O); 1H NMR
(400 MHz, DMSO-d6) d (ppm): 13.86 (s, 1H, OH), 9.42 (s,
1H, pyrazole ring-H), 8.03 (d, 1H, Ar–H), 7.93 (t, 3H, Ar–H),
7.79 (d, 1H, Hb, J = 15.10 Hz), 7.59 (t, 4H, Ar–H), 7.42 (d,
1H, Ar–H), 7.14 (d, 2H, Ar–H), 6.68 (d, 1H, Ha), 6.46 (d, 1H,
Ar–CH=C), 5.87 (m, 1H, Ar–C=CH), 4.92 (d, 2H, O–CH2),
0
(C5 ), 129.7 (Cb), 129.5 (Ar–C), 127.2 (C7), 126.9 (Ca),
124.2 (Ar–C), 121.1 (C3), 119.5 (C4), 119.3 (Ar–C), 118.9
0
(C6), 118.2 (Ar–C), 115.3 (C4 ), 114.5 (C4a), 114.3 (Ar–C),
110.3 (C8), 107.5 (Ar–C), 66.1 (C2-OCH2), 63.5 (OCH2),
14.8 (CH3); MS (m/z): 465 (M ? H)?; Elemental analysis
(C29H24N2O4); calcd. C, 74.98; H, 5.21; N, 6.03; found C,
74.96; H, 5.22; N, 6.00 %.
123