866 J. Chin. Chem. Soc., Vol. 58, No. 7, 2011
Abdel-Aziz et al.
1
volume of edema by 38.90% after 6 h with 79.67% potency
respect to the reference drug indomethacin.
(KBr) nmax/cm-1 1655 (2C=O), 1590 (C=N); H NMR
(DMSO-d6) d 2.36 (s, 3H, -CH3), 3.79 (s, 3H, -OCH3), 3.81
(s, 3H, -OCH3), 6.97-7.12 (m, 5H, ArH), 7.47-7.79 (m,
12H, ArH); 13C NMR d 11.96 (-CH3), 55.91 (2 -OCH3),
115.02, 115.10, 121.24, 122.68, 126.12, 126.20, 127.55,
127.68, 129.74, 130.05, 130.91, 131.23, 138.79, 142.6,
143.10, 144.44, 149.85, 161.76, 162.06, 184.78 (-C=O),
189.08 (-C=O); MS m/z (%) 478 (M+, 0.29), 281 (43.94),
207 (100), 73 (26.87). Anal. Calcd for C30H26N2O4
(478.54): C, 75.30; H, 5.48; N, 5.85. Found: C, 75.51; H,
5.66; N, 5.98.
EXPERIMENTAL
Melting points (°C, uncorrected) were determined us-
ing a Gallenkamp melting point apparatus. The IR spectra
(KBr) were recorded on a PerkinElmer FT/IR spectrome-
ter. The NMR spectra were recorded at 400 MHz on a Jeol
spectrometer using tetramethylsilane as an internal stan-
dard. 1H and 13C spectra were run at 400 and 100 MHz, re-
spectively. Chemical shift (d) values are given in parts per
million and coupling constants (J) in Hertz. The mass spec-
tra were performed using a Varian MAT CH-5 spectrometer
(70 eV). Microwave experiments were carried out using a
CEM microwave reactor, USA.
1,1¢-(5-Methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(3-(4-
chlorophenyl)prop-2-en-1-one) (3c)
White powder, 75% yield; mp 195-197 °C; IR (KBr)
nmax/cm-1 1662 (2C=O), 1598 (C=N); 1H NMR (DMSO-d6)
d 2.38 (s, 3H, CH3), 7.23-7.86 (m, 17H, ArH); MS m/z (%)
487 (M+, 0.95), 207 (100). Anal. Calcd for C28H20Cl2N2O2
(487.38): C, 69.00; H, 4.14; N, 5.75. Found: C, 69.17; H,
4.35; N, 5.91.
Synthesis of bis chalcones 3a-h
Microwave synthesis
To a solution of the appropriate pyrazole 2a,b (1
mmol) and the appropriate aldehyde (2 mmol) in ethanol
(10 mL), 10% aqueous sodium hydroxide (1 mL) was irra-
diated under microwave irradiation at 100W and 60 °C for
4 min. The reaction mixture was cooled. The resulting solid
was filtered off, washed with water, dried and crystallized
from EtOH/DMF to afford chalcones 3a-c.
1,1¢-(5-Methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(3-
(furan-2-yl)prop-2-en-1-one) (3d)
Beige powder, 70% yield; mp 187-189 °C; IR (KBr)
1
nmax/cm-1 1665, 1654 (2C=O), 1604 (C=N); H NMR
(DMSO-d6) d 2.36 (s, 3H, CH3), 6.66-6.69 (m, 2H, ArH),
6.90 (d, 1H, J = 15.88 Hz, ArH), 6.98 (d, 1H, J = 3.64 Hz,
ArH), 7.08 (d, 1H, J = 3.64 Hz, ArH), 7.35 (d, 1H, J = 15.88
Hz, ArH), 7.49-7.71 (m, 7H, ArH), 7.88 (d, 2H, J = 12.20
Hz, ArH); 13C NMR d 11.95 (-CH3), 112.54, 113.61,
113.78, 117.43, 118.33, 120.19, 125.15, 126.17, 129.56,
129.84, 129.92, 130.08, 130.65, 146.68, 147.07, 151.32,
151.46, 184.10 (-C=O), 188.25 (-C=O); MS m/z (%) 398
(M+, 3.1), 207 (100). Anal. Calcd for C24H18N2O4 (398.41):
C, 72.35; H, 4.55; N, 7.03. Found: C, 72.44; H, 4.72; N,
7.31.
Conventional synthesis
To a stirred solution of the appropriate pyrazole 2a,b
(10 mmol) and the appropriate aldehyde (20 mmol) in etha-
nol (30 mL), 10% aqueous sodium hydroxide (10 mL) was
added portion-wise at room temperature for 10 min, the re-
action mixture was further stirred for 12 h. The resulting
solid was filtered off, washed with water, dried and crystal-
lized from EtOH/DMF to afford chalcones 3a-c.
1,1¢-(5-Methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(3-
phenylprop-2-en-1-one) (3a)
Pale yellow crystals, 70% yield; mp 170-172 °C; IR
1,1¢-(5-Methyl-1-(4-tolyl)-1H-pyrazole-3,4-diyl)bis(3-
phenylprop-2-en-1-one) (3e)
1
(KBr) nmax/cm-1 1661 (2C=O), 1596 (C=N); H NMR
(DMSO-d6) d 2.38 (s, 3H, -CH3), 7.24-7.84 (m, 19H, ArH);
13C NMR d 11.98 (-CH3), 122.58, 123.59, 126.23, 128.36,
129.08, 129.29, 129.53, 129.62, 129.84, 130.07, 131.01,
131.39, 134.92, 135.14, 138.72, 142.83, 143.58, 144.47,
149.69, 184.80 (-C=O), 189.07 (-C=O); MS m/z (%) 418
(M+, 0.50), 281 (27.90), 207 (100), 73 (43.92). Anal. Calcd
for C28H22N2O2 (418.49): C, 80.36; H, 5.30; N, 6.69.
Found: C, 80.56; H, 5.21; N, 6.82.
Pale yellow crystals, 88% yield; mp 156-158 °C; IR
1
(KBr) nmax/cm-1 1662 (2C=O), 1598 (C=N); H NMR
(DMSO-d6) d 2.36 (s, 3H, -CH3), 2.43 (s, 3H, -CH3),
7.23-7.83 (m, 18H, ArH); 13C NMR d 11.95 (-CH3), 21.30
(-p-CH3), 122.48, 123.62, 126.04, 128.36, 129.08, 129.27,
129.53, 129.63, 130.45, 131.00, 131.39, 134.92, 135.14,
136.29, 139.57, 142.77, 143.54, 144.41, 149.56, 184.81
(-C=O), 189.07 (-C=O); MS m/z (%) 432 (M+, 0.46), 281
(28.18), 207 (100), 73 (52.93). Anal. Calcd for C29H24N2O2
(432.51): C, 80.53; H, 5.59; N, 6.48. Found: C, 80.71; H,
5.82; N, 6.69.
1,1¢-(5-Methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(3-(4-
methoxyphenyl)prop-2-en-1-one) (3b)
Pale yellow crystals, 78% yield; mp 121-125 °C; IR