Med Chem Res
1
300 MHz) δ / ppm: 187.7 (C=O, C-1), 121.2, 145.1
(CH=CH, C-2, C-3), 128.9 (C-Br), 125.3, 128.3, 125.4,
125.3, 125.6, 121.6, 128.3, 125.2, 125.9, 123.5 (13 CH
aromatic, C-1ʹ, C-2ʹ, C-3ʹ, C-4ʹ, C-5ʹ, C-6ʹ, C-7ʹ, C-8ʹ, C-10ʹ,
C-2ʺ, C-3ʺ, C-5ʺ, C-6ʺ), 133.1, 136.0 (2C aromatic, C-9, C-
1ʺ); Mass (m/z) (M+) 387, (M+ 2) 389; Anal. Calcd for C,
71.33; H, 3.90, Found: C, 71.36; H, 3.87.
1541.31 (C=C str), 724.34 (C-Cl); H NMR (400 MHz,
DMSO, δ/ppm): 2.34 (s, 3H, CH3), 3.94 (dd, 1H, HA, JAB
18.1, JAx 9.5), 3.69 (dd, 1H, HB, JAB 18, JBx 9.51), 3.9
(dd, 1H, Hx, JAx 11.0, JBx 9.52), 6.83 to 7.98 (m, 11H,
Ar–H); 13C NMR (300 MHz, CDCl3) δ /ppm: 144.7, 151.7
(C=N), 136.6 (C-Cl), 137.6 (C–CH3), 128.7, 127.6, 128.5,
127.6, 126.4, 128.4, 127.8, 129.6, 127.5, 124.6, 126.3,
124.2 (12 CH aromatic, C-2ʺ, C-3ʺ, C-5ʺ, C-6ʺ, C-3ʺʹ, C-4ʺʹ,
C-5ʺʹ, C-1ʺʺ, C-2ʺʺ, C-4ʺʺ, C-5ʺʺ), 134.3, 127.6, 141.1 (3C
aromatic, C-1ʺ, C-2ʺʹ, C-6ʺʺ); Mass (FAB), m/z: (M+) 411;
Anal. Calcd for C, 61.23; H, 4.40; Found: C, 61.24; H, 4.42.
3-(Anthracen-9-yl)-1-(4-fluorophenyl)prop-2-en-1-one (3c)
Dark Red Crystals (EtOH). This compound was prepared
by condensing 9-anthraldehyde with substituted acet-
ophenones; m.p.122–124 °C; yield 74%; IR (KBr) cm−1
:
3041, 3007 (CH str), 1696 (α,β unsaturated keto group),
1504 (C=C str), 1338(C–F). 1H NMR (CDCl3, 400 MHz) δ
/ ppm: 7.41–7.43 (d, 1H, J = 15.0 Hz, H-2), 7.53–7.54 (d,
1H, J = 15.3 Hz, H-3), 7.22–7.25 (d, 1H, J = 8.6 Hz,
Ar–H), 7.42–7.45 (d, 1H, J = 8.5 Hz, Ar–H), 7.92–8.16 (m,
4H, Ar–H), 8.25–8.29 (m, 6H, Ar–H), 8.29 (s, 1H, Ar–H);
13C NMR (CDCl3, 300 MHz) δ / ppm: 187.7 (C=O, C-1),
121.2, 145.1 (CH=CH, C-2, C-3), 168.7 (C-F), 125.4,
128.5, 126.4, 123.3, 121.4, 127.2, 124.2, 126.6, 124.2 (13
CH aromatic, C-1ʹ, C-2ʹ, C-3ʹ, C-4ʹ, C-5ʹ, C-6ʹ, C-7ʹ, C-8ʹ,
C-10ʹ, C-2ʺ, C-3ʺ, C-5ʺ, C-6ʺ), 133.4, 136.8 (2C aromatic,
C-9, C-1ʺ); Mass (m/z) (M+ 1) 327; Anal. Calcd for C,
84.64; H, 4.63, Found: C, 84.60; H, 4.65.
2-(3-(4-Bromophenyl)-1-tosyl-4,5-dihydro-1H-pyrazol-5-yl)
pyridine (4b)
Yellow Crystals (EtOH). This compound was obtained by
condensing substituted 4-bromo chalcones with p-tolue-
nesulfonylhydrazide; m.p.167–169 °C; yield 81 %; IR
(KBr, cm−1): 3114.56 (aromatic CH str), 1650.45 (C=N
str), 1541.31 (C=C str), 724.34 (C-Cl); 1H NMR (400
MHz, DMSO, δ/ppm): 2.34 (s, 3H, CH3), 3.94 (dd, 1H,
HA, JAB 18.1, JAx9.5), 3.69 (dd, 1H, HB, JAB 18, JBx
9.51), 3.9 (dd, 1H, Hx, JAx 11.0, JBx 9.52), 6.83 to 7.98
(m, 12H, Ar–H); 13C NMR (300 MHz, CDCl3) δ /ppm:
151.7, 144.7 (C=N),125.6 (C–Br), 137.6 (C–CH3), 128.7,
127.6, 128.5, 127.6, 126.4, 128.4, 127.8, 129.6, 127.5,
124.6, 126.3, 124.2 (11 CH aromatic, C-2ʺ, C-3ʺ, C-5ʺ, C-
6ʺ, C-3ʺʹ, C-4ʺʹ, C-5ʺʹ, C-1ʺʺ, C-2ʺʺ, C-4ʺʺ, C-5ʺʺ), 134.3,
127.6, 141.1 (3C aromatic, C-1ʺ, C-2ʺʹ, C-6ʺʺ); Mass
(FAB), m/z: (M+) 456; Anal. Calcd for C, 55.27; H, 3.98;
Found: C, 55.28; H, 3.99.
3-(Anthracen-9-yl)-1-(4-aminophenyl)prop-2-en-1-one (3d)
Light Yellow Crystals (EtOH). This compound was pre-
pared by condensing 9-anthraldehyde with substituted
acetophenones; m.p.132–135 °C; yield 76%; IR (KBr)
cm−1: 3012 (CH str), 1693(α,βunsaturated keto group),
1514 (C=C str), 3512, 3215 (NH2). 1H NMR (CDCl3, 400
MHz) δ / ppm: 7.45–7.47 (d, 1H, J = 15.2 Hz, H-2), 7.48-
7.49 (d, 1H, J = 15.0 Hz, H-3), 7.12-7.14 (d, 1H, J = 8.1
Hz, Ar–H), 7.41–7.44 (d, 1H, J = 8.5 Hz, Ar–H), 7.88–7.92
(m, 4H, Ar–H), 8.13–8.17 (m, 6H, Ar–H), 8.1 (s, 1H,
Ar–H); 13C NMR (CDCl3, 300 MHz) δ / ppm: 187.7 (C=O,
C-1), 121.2, 145.1 (CH=CH, C-2, C-3), 154.2 (C-NH2),
122.4, 128.3, 126.2, 125.3, 126.4, 127.5, 124.2, 126.2,
126.5, 124.5 (13 CH aromatic, C-1ʹ, C-2ʹ, C-3ʹ, C-4ʹ, C-5ʹ,
C-6ʹ, C-7ʹ, C-8ʹ, C-10ʹ, C-2ʺ, C-3ʺ, C-5ʺ, C-6ʺ), 135.4, 135.4
(2C aromatic, C-9, C-1ʺ).; Mass (m/z) (M+) 228; Anal.
Calcd for C, 85.42; H, 5.30, Found: C, 85.43; H, 5.46.
2-(3-(4-Fluorophenyl)-1-tosyl-4,5-dihydro-1H-pyrazol-5-
yl)pyridine (4c)
Light Red Crystals (EtOH). This compound was obtained
by condensing substituted 4-fluoro chalcones with p-
toluenesulfonylhydrazide; m.p.154–156 °C; yield 78%; IR
(KBr, cm−1): 3136.78 (aromatic CH str), 1643.23 (C=N
1
str), 1534.35 (C=C str), 1372.14 (C–F); H NMR (400
MHz, DMSO, δ/ppm): 2.34 (s, 3H, CH3), 4.02 (dd, 1H,
HA, JAB 18.11, JAx 9.1), 3.43 (dd, 1H, HB, JAB 18.3,
JBx 9.71), 3.24 (dd, 1H, Hx, JAx 11.5, JBx 9.21), 7.05 to
7.79 (m, 12H, Ar–H); 13C NMR (300 MHz, CDCl3, δ/
ppm): 144.4, 151.3 (C=N), 165.8 (C–F), 137.3 (C–CH3),
128.2, 127.8, 128.4, 126.2, 126.3, 127.6, 128.4, 128.5,
128.7, 128.6, 126.9 (11 CH aromatic, C-2ʺ, C-3ʺ, C-5ʺ, C-
6ʺ, C-3ʺʹ, C-4ʺʹ, C-5ʺʹ, C-1ʺʺ, C-2ʺʺ, C-4ʺʺ, C-5ʺʹ), 133.5,
127.5, 142.2 (3C aromatic, C-1ʺ, C-2ʺʹ, C-6ʺʺ); Mass
(FAB), m/z: (M+) 395; Anal. Calcd for C, 63.78; H, 4.59;
Found: C, 63.77; H, 4.60.
2-(3-(4-Chlorophenyl)-1-tosyl-4,5-dihydro-1H-pyrazol-5-
yl)pyridine (4a)
Yellow Crystals (EtOH). This compound was obtained by
condensing substituted 4-chloro chalcones with p-toluene-
sulfonylhydrazide; m.p.167–169 °C; yield 81%; IR (KBr,
cm−1): 3114.56 (aromatic CH str), 1650.45 (C=N str),