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Med Chem Res (2017) 26:2127–2140
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63.0, 61.9, 45.9, 44.1. MS m/z: 337.08 (M+•, 100%),
310.99 (M+• + 2–28, 55%).
cm−1 3333, 3068, 1693, 1500, 1271, 705. H NMR (300
MHz, CDCl3) δH: 9.43 (s, 1H, OH), 6.94 (d, 1H, ArH),
6.77–6.82 (m, 3H, ArH), 6.57 (dd, 1H, ArH), 5.72 (dd, J
3.6, 12Hz, 1H, Hx), 3.88 (dd, J 11.4, 17.4Hz, 1H, Hb), 3.86
(s, 2H, Hc), 3.84 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 3.32
(dd, J 3.6, 18 Hz, 1H, Ha), 13C NMR (100 MHz, DMSO-d6)
δC: 187.0, 177.1, 175.8, 161.9, 157.2, 156.5, 142.9, 132.9,
129.8, 128.9, 127.8, 126.8, 125.5, 73.7, 63.0, 61.8, 45.9,
44.1. MS m/z 388.79 (M+• + 1, 12%), 325.19 (M+•-63,
88%).
2-[3-(4-Hydroxyphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-
1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5b)
Pale yellow powder; yield, 46%; purity, 95.40% (HPLC,
methanol: water, 80:20); mp 200–202 °C. IR, νmax (KBr)/
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cm−1 3317, 3064, 2960, 1739, 1504, 1321, 719. H NMR
(300 MHz, CDCl3) δH: 9.73 (s, 1H, OH), 7.41–7.47 (m, 1H,
ArH), 7.10–7.31 (m, 3H, AHr), 6.93 (m, 2H, ArH), 6.86
(dd, 2H, ArH), 5.75 (dd, J 3.9, 11.1, Hx), 3.96 (dd, J 11.1,
17.7, Hb), 3.89 (s, 2H, Hc), 3.78 (s, 3H, OCH3), 3.53 (dd, J
4.2, 18, Ha). 13C NMR (100 MHz, DMSO-d6) δC: 186.7,
177.1, 175.8, 160.9, 157.2, 156.5, 156.3, 142.9, 140.5,
132.9, 132.1, 129.2, 128.5, 126.8, 63.0, 61.9, 45.9, 44.1.
MS m/z 388.99 (M+• + Na, 100%), 366.99 (M+•, 97%).
2-[5-(4-Bromophenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-
1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5f)
Brown powder; yield 62%; purity, 91.19% (HPLC,
methanol: water, 80:20); mp 219–221 °C. IR, νmax (KBr)/
cm−1 3333, 3068, 1693, 1518, 1139, 746, 551. H NMR
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(300 MHz, CDCl3) δH: 9.39 (s, 1H, OH), 7.63 (d, 1H, ArH),
7.22–7.37 (m, 5H, ArH), 6.94 (d, 1H, ArH), 6.57 (dd, 1H,
ArH), 5.77 (dd, J 3.6, 11.1, 1H, Hx), 3.90 (dd, J 10.9, 17.5,
2-[5-(2,4-Dibromophenyl)-3-(4-hydroxyphenyl)-4,5-
dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5c)
1H, Hb), 3.86 (s, 2H, Hc), 3.32 (dd, J 3.6, 17.7, 1H, Ha), 13
C
Pale brown powder; yield, 57%; purity, 93.06% (HPLC,
NMR (100 MHz, DMSO-d6) δC: 186.8, 176.7, 161.2, 157.1,
150.0, 132.9, 129.2, 127.7, 126.6, 119.7, 116.9, 115.9,
112.4, 63.5, 59.5, 45.6. MS m/z 414.99 (M+•, 25%), 332.99
(M+•-81, 100%).
methanol:water, 80:20); mp 234–236 °C. IR, νmax (KBr)/
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cm−1 3302, 3066, 1695, 1502, 1327, 1004, 725, 534. H
NMR (300 MHz, CDCl3) δH: 9.13 (s, 1H, OH), 7.11–7.63
(m, 5H, ArH), 6.95 (dd, 1H, ArH), 6.58 (dd, 1H, ArH), 5.73
(dd, J 3.8, 11.2, 1H, Hx), 3.91 (dd, J 11.4, 18.6, 1H, Hb),
3.86 (s, 2H, Hc), 3.28 (dd, J 3.8, 18, 1H, Ha). 13C NMR
(100 MHz, DMSO-d6) δC: 189.7, 173.0, 172.9, 165.7,
161.9, 159.4, 158.5, 131.8, 131.4, 129.1, 128.7, 128.3,
127.5, 118.4, 117.0, 62.3, 55.9, 35.6. MS m/z 493.00 (M+•,
19%), 472.29 (M+•-17, 100%).
2-[5-(Furan-3-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-
pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5g)
Pale yellow powder; yield, 68%; purity, 97.31% (HPLC,
methanol:water, 80:20); mp 210–212 °C. IR, νmax (KBr)/
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cm−1 3344, 3053, 1730, 1518, 1268, 705. H NMR (300
MHz, CDCl3) δH: 9.66 (s, 1H, OH), 7.32–7.48 (m, 3H,
ArH), 6.98–7.12 (m, 2H, ArH), 6.59 (d, 1H, ArH), 6.34 (dd,
1H, ArH), 5.87 (dd, J 4.8, 10.5 Hz, 1H, Hx), 3.92 (s, 2H,
Hc), 3.83 (dd, J 5.1, 9.0 Hz, 1H, Hb), 3.74 (dd, J 4.8, 15.9
Hz, 1H, Ha), 13C NMR (100 MHz, DMSO-d6) δC: 186.6,
177.1, 160.8, 157.2, 150.5, 142.8, 132.8, 129.0, 119.5,
116.8, 115.6, 110.5, 108.6, 65.5, 56.5, 41.7. MS m/z 327.99
(M+•, 87%), (M+•-116, 100%).
2-[3-(4-Hydroxyphenyl)-5-(thiophen-3-yl)-4,5-dihydro-1H-
pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5d)
Pale yellow powder; yield, 62%; purity, 91.01% (HPLC,
methanol:water, 80:20); mp 284–286 °C. IR, νmax (KBr)/
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cm−1 3333, 3068, 1693, 1500, 1271, 705. H NMR (300
MHz, CDCl3) δH: 10.27 (s, 1H, OH), 7.74 (dd, 1H, ArH),
7.42–7.47 (m, 2H, ArH), 7.11 (d, 1H, ArH), 6.93–7.00 (m,
3H, ArH), 6.05 (dd, J 3.3, 10.9, 1H, Hx), 4.16 (dd, J 10.8,
18.7, 1H, Hb), 3.96 (s, 2H, Hc), 3.67 (dd, J 3.3, 18.9, 1H,
Ha). 13C NMR (100 MHz, DMSO-d6) δC: 188.7, 174.0,
164.7, 162.9, 159.4, 158.5, 131.8, 131.4, 129.1, 128.5,
127.6, 118.4, 117.3, 62.3, 62.3, 55.91, 35.6. MS m/z 343.09
(M+•, 100%).
2-[5-(2,4-Dinitrophenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-
1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5h)
Light brown powder; yield, 57%; purity, 96.78% (HPLC,
methanol:water, 80:20); mp 265–268 °C. IR, νmax (KBr)/
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cm−1 3315, 3049, 1687, 1695, 1497, 1259, 759. H NMR
(300 MHz, CDCl3) δH: 9.63 (s, 1H, OH), 8.04–8.21 (m, 3H,
ArH), 7.67–7.72 (m, 2H, ArH), 7.17 (d, 1H, ArH), 6.73 (dd,
1H, ArH), 5.96 (dd, J 4.2, 12, 1H, Hx), 4.08 (dd, J 11.5,
18.0, 1H, Hb), 3.96 (s, 2H, Hc), 3.44 (dd, J 4.8, 18.0, 1H,
Ha). 13C NMR (100 MHz, DMSO-d6) δC: 186.4, 176.8,
162.0, 160.4, 159.5, 157.4, 157.2, 132.7, 130.4, 130.3,
2-[5-(Furan-3-yl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-4,5-
dihydro-1H-pyrazol-1-yl]-1,3-thiazol-4(5H)-one (5e)
Brown powder; yield, 65%; purity, 96.33% (HPLC,
methanol: water, 80:20); mp 247–249 °C. IR, νmax (KBr)/