Med Chem Res (2012) 21:2990–2997
2995
[4,5-Dihydro-5-(2,5-dimethoxyphenyl)-3-(naphth-2-yl)-
1H-pyrazol-1-yl]-ethanone (62)
7.40–7.61 (m, 4H), 7.28 (m, 1H), 6.16 (dd, 1H, J = 4.8 and
11.7 Hz), 4.13 (dd, 1H, J = 12.00 and 18.00 Hz), 3.28 (dd,
1H, J = 4.8 and 18.00 Hz), 2.52 (3H, s). Anal. Calcd for
C21H17N3O3: C 70.18, H 4.77, N 11.69. Found: C 70.39, H
4.59, N 11.98.
White powder, Yield 81%. Mp 164–166°C. I.R (KBr, cm-1):
1,662, 1,511, 1,216. H NMR (CDCl3, 300 MHz): 8.04 (d,
1
J = 1.5 Hz, 1H), 7.80–7.90 (m, 4H), 7.48–7.53 (m, 2H),
6.74–6.85 (m, 2H), 6.62 (d, J = 2.8 Hz, 1H), 5.87 (dd,
J = 4.5 and 11.7 Hz, 1H), 3.89 (s, 3H), 3.76 (s, 3H), 3.82
(dd, J = 11.7 and 17.7 Hz, 1H), 3.16 (dd, J = 4.5 and
17.7 Hz, 1H), 2.61 (s, 3H). 13C NMR (CDCl3, 75.47 MHz):
168.83, 154.71, 153.75, 150.27, 134.11, 133.02, 130.59,
129.27, 128.40, 127.87, 127.14, 127.06, 126.69, 123.34,
112.53, 112.21, 111.93, 56.09, 55.73, 55.66, 41.49, 22.05.
Calcd for C23H22N2O3: C 73.78, H 5.92, N 7.48. Found: C
74.02, H 5.69, N 7.81.
[4,5-Dihydro-3-(naphth-2-yl)-5-(2,3-dichlorophenyl)-1H-
pyrazol-1-yl]-ethanone (59)
White powder, Yield 90%. Mp 184–186°C. I.R (KBr,
1
cm-1): 1,660, 1,600, 776. H NMR (CDCl3, 300 MHz):
8.04 (d, J = 8.4 Hz, 1H), 7.84–7.89 (m, 4H), 7.50–7.53
(m, 2H), 7.37 (d, J = 7.2 Hz, 1H), 7.16 (t, J = 7.8 Hz,
1H), 7.00 (d, J = 7.5 Hz, 1H), 5.96 (dd, J = 4.5 and
11.7 Hz, 1H), 3.96 (dd, J = 11.7 and 17.7 Hz, 1H), 3.16
(dd, J = 4.5 and 17.7 Hz, 1H), 2.53 (s, 3H). 13C NMR
(CDCl3, 75.47 MHz): 168.96, 154.26, 140.86, 134.33,
133.77, 132.97, 130.06, 129.54, 128.68, 128.58, 128.43,
127.89, 127.76, 127.40, 127.29, 126.87, 123.99, 123.14,
58.34, 41.29, 21.96. Anal. Calcd for C21H16Cl2N2O: C
65.81, H 4.21, N 7.31. C 66.12, H 4.02, N 7.58.
[4,5-Dihydro-5-(3,4-dimethoxyphenyl)-3-(naphth-2-yl)-
1H-pyrazol-1-yl]-ethanone (63)
White powder, Yield 75%. Mp 165–166°C. I.R (KBr, cm-1):
1,670, 1,593, 1,312, 1,240, 1,137. 1H NMR (CDCl3,
300 MHz): 8.11 (dd, J = 1.5 and 8.6 Hz, 1H), 7.83–7.94 (m,
4H), 7.51–7.56 (m, 2H), 6.73–6.81 (m, 3H), 5.60 (dd,
J = 4.5 and 11.7 Hz, 1H), 3.85 (s, 3H), 3.84 (s, 3H), 3.62
(dd, J = 11.7 and 17.7 Hz, 1H), 3.11 (dd, J = 4.5 and
17.7 Hz, 1H), 2.56 (s, 3H). 13C NMR (CDCl3, 75.47 MHz):
168.89, 153.87, 149.25, 148.51, 134.58, 134.12, 132.98,
129.02, 128.49, 128.36, 127.84, 127.23, 127.07, 126.76,
123.24, 117.62, 111.50, 109.13, 59.86, 55.90, 42.28, 22.01.
Anal. Calcd for C23H22N2O3: C 73.78, H 5.92, N 7.48.
Found: C 74.09, H 5.67, N 7.87.
[4,5-Dihydro-5-(3,4,5-trimethoxyphenyl)-3-(naphth-2-yl)-
1H-pyrazol-1-yl]-ethanone (60)
White powder, Yield 74%. Mp 140–143°C. I.R (KBr, cm-1):
2,968, 1,660, 1,592, 1,507, 1,242, 1,126. 1H NMR (CDCl3,
300 MHz): 8.04 (d, J = 8.1 Hz, 1H), 7.94 (m, 2H), 7.69 (m,
2H), 7.41 (m, 2H), 6.50 (s, 2H), 5.46 (dd, J = 4.8 and
11.7 Hz, 1H), 3.92 (s, 6H), 3.87 (s, 3H), 3.22 (dd, J = 4.8
and 17.7 Hz, 1H), 3.82 (dd, J = 11.7 and 17.7 Hz, 1H), 2.19
(s, 3H). 13C NMR (CDCl3, 75.47 MHz): 169.04, 154.07,
153.68, 137.72, 137.43, 134.19, 133.01, 128.93, 128.56,
128.41, 127.89, 127.34, 127.20, 126.85, 123.26, 102.42,
60.75, 60.34, 56.14, 42.50, 22.05. Anal. Calcd for
C24H24N2O4: C 71.27, H 5.98, N 6.93. Found: C 71.54, H
5.67, N 7.12.
[4,5-Dihydro-5-(3-hydroxy-4-methoxyphenyl)-3-(naphth-2-
yl)-1H-pyrazol-1-yl]-ethanone (64)
White powder, Yield 78%. Mp 182–186°C. I.R (KBr,
1
cm-1): 3,326, 1,657, 1,257. H NMR (CDCl3, 300 MHz):
8.06 (d, J = 8.7 Hz,1H), 7.85–7.92 (m, 4H), 7.57–7.54 (m,
2H), 6.76–6.80 (m, 3H), 5.55 (dd, J = 3.9 and 11.7 Hz,
1H), 3.85 (s, 3H), 3.79 (dd, J = 11.7 and 17.4 Hz, 1H),
3.28 (dd, J = 3.9 and 17.4 Hz, 1H), 2.45 (s, 3H). 13C NMR
(CDCl3, 75.47 MHz): 151.46, 146.03, 135.32, 133.00,
128.45, 128.36, 127.83, 127.16, 127.02, 126.70, 123.28,
117.54, 111.54, 110.75, 59.67, 55.96, 42.28, 22.00. Anal.
Calcd for C22H20N2O3: C 73.32, H 5.59, N 7.77. Found: C
73.68, H 5.36, N 7.91.
[4,5-Dihydro-5-(2,3,4-trimethoxyphenyl)-3-(naphth-2-yl)-
1H-pyrazol-1-yl]-ethanone (61)
White powder, Yield 73%. Mp 170–171°C. I.R (KBr,
1
cm-1): 3,000, 1,668, 1,601, 1,496, 1,230, 1,094. H NMR
(CDCl3, 300 MHz): 8.04 (d, J = 1.2 Hz, 1H), 7.82–7.89
(m, 4H), 7.46–7.51 (m, 2H), 6.95 (d, J = 8.1 Hz, 1H), 6.65
(d, J = 8.1 Hz, 1H), 5.70 (dd, J = 4.8 and 11.7, 1H), 3.85
(s, 6H), 3.79 (s, 3H), 3.62 (dd, J = 11.7 and 17.4 Hz, 1H),
2.99 (dd, J = 4.8 and 17.4 Hz, 1H), 2.37 (s, 3H). 13C NMR
(CDCl3, 75.47 MHz): 168.66, 150.57, 149.62, 149.33,
143.18, 134.03, 133.27, 127.69, 126.69, 120.72, 111.01,
98.18, 56.80, 56.45, 56.24, 56.17, 41.52, 21.87. Anal.
Calcd for C24H24N2O4: C 71.27, H 5.98, N 6.93. Found: C
71.48, H 5.77, N 7.08.
[5-(3-Bromophenyl)-4,5-dihydro-3-(naphth-2-yl)-1H-
pyrazol-1-yl]-ethanone (65)
White powder, Yield 83%. Mp 167–169°C. I.R (KBr,
cm-1): 3,042, 1,656, 1,604, 1,592, 1,146. 1H NMR (CDCl3,
300 MHz): 8.06 (d, J = 8.7 Hz, 1H), 7.83–7.92 (m, 4H),
123