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6783
127.2 (d), 113.8 (2 Â d), 55.5 (q), 21.2 (2 Â q), 21.1 (q). ESI-MS m/z:
4.2.15. (E)-3-(4-Chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-
1-one (4o)
281 [M+H]+, 302 [M+Na]+, 582 [2M+Na]+.
White solid (0.68 g, 2.49 mmol, 50% yield). Mp 86–88 °C [lit.28
90–93 °C]. IR (KBr disk): 3063, 2931, 1652, 1600, 1257,
4.2.10. (E)-3-(2,4-Dimethoxyphenyl)-1-(4-
methoxyphenyl)prop-2-en-1-one (4j)
1100 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.16 (d, J = 15.7 Hz, 2H),
.
Pale yellow solid (1.47 g, 4.93 mmol, 99% yield). Mp 80–82 °C
8.04 (d, J = 8.9 Hz, 1H), 7.74 (m, 1H), 7.50 (d, J = 15.7 Hz, 1H),
7.34 (m, 3H), 7.00 (d, J = 8.9 Hz, 2H), 3.90 (s, 3H). 13C NMR
(50 MHz, CDCl3) d 188.7 (s), 163.5 (s), 139.8 (d), 135.4 (s), 133.5
(s), 131.0 (2 Â d), 130.3 (d), 127.8 (d), 127.0 (d), 124.7 (d), 113.9
(2 Â d), 55.5 (q). ESI-MS m/z: 273 [M+H]+, 294 [M+Na]+, 566
[2M+Na]+.
[lit.23 83–85 °C]. IR (KBr disk): 3063, 2932, 1644, 1601,
1280 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.05 (d, J = 15.6 Hz, 1H),
.
8.03 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 15.6 Hz, 1H), 7.57 (d, J = 8.6 Hz,
1H), 6.96 (d, J = 8.6 Hz, 2H), 6.53 (dd, J1 = 8.4, J2 = 2.3 Hz, 1H),
6.47 (d, J = 2.3 Hz, 1H), 3.89 (s, 3H), 3.87 (s, 3H), 3.85 (s, 3H). 13C
NMR (50 MHz, CDCl3) d 189.4 (s), 163.0 (s), 162.8 (s), 160.3 (s),
139.7 (d), 131.7 (s), 130.8 (d), 130.7 (2 Â d), 120.2 (d), 117.3 (s),
113.7 (2 Â d), 105.3 (d), 98.4 (d), 55.5 (2 Â q), 55.4 (q). ESI-MS m/
z: 299 [M+H]+.
4.2.16. (E)-1-(4-Methoxyphenyl)-3-(1H-pyrrol-2-yl)prop-2-en-
1-one (4p)
Green solid (0.88 g, 3.87 mmol, 78% yield). Mp 164–166 °C [lit.13
164 °C]. IR (KBr disk): 3233, 3087, 2964, 1650, 1604, 1542,
4.2.11. (E)-1-(4-Methoxyphenyl)-3-(4-methoxyphenyl)prop-2-
en-1-one (4k)
1241 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.88 (br s, 1H), 8.00 (d,
.
J = 9.0 Hz, 2H), 7.73 (d, J = 15.5 Hz, 1H), 7.16 (d, J = 15.5 Hz, 1H),
6.96 (d, J = 9.0 Hz, 2H), 6.95 (m, 1H), 6.70 (m, 1H), 6.32 (m, 1H),
3.88 (s, 3H). 13C NMR (50 MHz, CDCl3) d 187.8 (s), 162.8 (s),
133.7 (d), 131.4 (s), 130.3 (2 Â d), 129.5 (s), 123.2 (d), 115.7 (d),
114.9 (d), 113.6 (2 Â d), 110.4 (d), 55.3 (q). ESI-MS m/z: 228
[M+H]+, 249 [M+Na]+.
Pale yellow solid (1.22 g, 4.54 mmol, 80% yield). Mp 98–100 °C
[lit.23 97–99 °C]. IR (KBr disk): 3071, 2960, 1654, 1594,
1253 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.03 (d, J = 8.9 Hz, 2H),
.
7.80 (d, J = 15.5 Hz, 1H), 7.60 (d, J = 8.7 Hz, 2H), 7.42 (d,
J = 15.5 Hz, 1H), 7.00 (dd, J1 = 8.9, J2 = 8.7 Hz, 4H), 3.90 (s, 3H),
3.84 (s, 3H). 13C NMR (50 MHz, CDCl3) d 188.7 (s), 163.2 (s),
161.5 (s), 143.8 (d), 131.3 (s), 130.7 (2 Â d), 130.1 (2 Â d), 127.7
(s), 119.5 (d), 114.3 (2 Â d), 113.7 (2 Â d), 55.5 (q), 55.4 (q). ESI-
MS m/z: 269 [M+H]+, 290 [M+Na]+, 558 [2M+Na]+.
4.2.17. (E)-1-(4-Hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-
1-one (4q)
Pale yellow solid (0.59 g, 2.47 mmol, 50% yield). Mp 178–180 °C
[lit.29 183–185 °C]. IR (KBr disk): 3112, 2944, 1646, 1589,
1226 cmÀ1 1H NMR (200 MHz, DMSO-d6) d 10.3 (s, 1H), 8.07 (d,
.
4.2.12. (E)-3-(4-Ethoxyphenyl)-1-(4-methoxyphenyl)prop-2-en-
1-one (4l)
J = 8.7 Hz, 2H), 7.86 (d, J = 15.6 Hz, 1H), 7.76 (d, J = 8.1 Hz, 2H),
7.66 (d, J = 15.6 Hz, 1H), 7.26 (d, J = 8.1 Hz, 2H), 6.91 (d, J = 8.7 Hz,
2H), 2.35 (s, 3H). 13C NMR (50 MHz, DMSO-d6) d 187.0 (s), 162.0
(s), 142.7 (d), 140.2 (s), 132.1 (s), 131.0 (2 Â d), 129.4 (2 Â d),
129.1 (s), 128.6 (2 Â d), 121.0 (s), 115.3 (2 Â d), 21.0 (q). ESI-MS
m/z: 239 [M+H]+, 260 [M+Na]+, 498 [2M+Na]+.
Pale yellow solid (0.70 g, 2.47 mmol, 50% yield). Mp 106–108 °C
[lit.13 105–107 °C]. IR (KBr disk): 3063, 2936, 1654, 1596,
1254 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.03 (d, J = 8.9 Hz, 2H),
.
7.77 (d, J = 15.6 Hz, 1H), 7.60 (d, J = 8.8 Hz, 2H), 7.42 (d,
J = 15.6 Hz, 1H), 6.97 (d, J = 8.9 Hz, 2H), 6.91 (d, J = 8.8 Hz, 2H),
4.07 (c, J = 7.0 Hz, 2H), 3.88 (s, 3H), 1.43 (t, J = 7.0 Hz, 3H). 13C
NMR (50 MHz, CDCl3) d 188.7 (s), 163.2 (s), 160.9 (s), 143.9 (d),
131.4 (s), 130.7 (2 Â d), 130.1 (2 Â d), 127.6 (s), 119.4 (d), 114.8
(2 Â d), 113.8 (2 Â d), 63.6 (t), 55.5 (q), 14.7 (q). ESI-MS m/z: 283
[M+H]+, 304 [M+Na]+, 586 [2M+Na]+.
4.2.18. (E)-1-(4-Hydroxyphenyl)-3-(2,4,6-
trimethylphenyl)prop-2-en-1-one (4r)
Pale yellow solid (1.13 g, 4.25 mmol, 85%). Mp 144–146 °C [lit.29
145–147 °C]. IR (KBr disk): 3116, 3067, 2976, 1643, 1604,
1211 cmÀ1 1H NMR (200 MHz, DMSO-d6) d 10.4 (s, 1H), 7.98 (d,
.
J = 8.8 Hz, 2H), 7.78 (d, J = 16.0 Hz, 1H), 7.33 (d, J = 16.0 Hz, 1H),
6.94 (s, 2H), 6.90 (d, J = 8.8 Hz, 2H), 2.34 (s, 6H), 2.25 (s, 3H). 13C
NMR (50 MHz, DMSO-d6) d 187.1 (s), 162.1 (s), 140.6 (d), 137.6
(s), 136.6 (2 Â d), 131.2 (s), 131.0 (2 Â d), 128.9 (3 Â s), 126.9 (d),
115.4 (2 Â d), 21.0 (2 Â q), 20.6 (q). ESI-MS m/z: 267 [M+H]+, 288
[M+Na]+, 554 [2M+Na]+.
4.2.13. (E)-1-(4-Methoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-
one (4m)
Pale brown solid (1.18 g, 4.16 mmol, 84% yield). Mp 160–162 °C
[lit.28 164 °C]. IR (KBr disk): 3079, 2932, 1657, 1596, 1513,
1264 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.72 (d, J = 8.9 Hz, 2H),
.
8.06 (d, J = 9.0 Hz, 2H), 7.82 (d, J = 15.8 Hz, 1H), 7.78 (d, J = 8.9 Hz,
2H), 7.65 (d, J = 15.8 Hz, 1H), 7.00 (d, J = 8.9 Hz, 2H), 3.90 (d,
J = 9.00 Hz, 2H), 4.00 (s, 3H). 13C NMR (50 MHz, CDCl3) d 187.8
(s), 163.9 (s), 141.3 (s), 140.7 (d), 131.0 (2 Â d), 130.4 (s), 128.8
(2 Â d), 128. 6 (s), 125.6 (d), 124.2 (2 Â d), 114.0 (2 Â d), 55.6 (q).
ESI-MS m/z: 284 [M+H]+.
4.2.19. (E)-1-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-
en-1-one (4s)
Pale yellow solid (0.72 g, 2.85 mmol, 57%). Mp 168–170 °C [lit.29
166 °C]. IR (KBr disk): 3148, 3047, 2980, 1645, 1600, 1219 cmÀ1. 1H
NMR (200 MHz, DMSO-d6) d 10.4 (s, 1H), 8.08 (d, J = 8.8 Hz, 2H),
7.83 (d, J = 8.8 Hz, 2H), 7.75 (d, J = 16.0 Hz, 1H), 7.66 (d,
J = 16.0 Hz, 1H), 7.01 (d, J = 8.8 Hz, 2H), 6.92 (d, J = 8.8 Hz, 2H),
3.82 (s, 3H). 13C NMR (50 MHz, DMSO-d6) d 187.0 (s), 162.0 (s),
161.1 (s), 142.6 (d), 131.0 (2 Â d), 130.5 (2 Â d), 129.3 (s), 127.5
(s), 119.6 (d), 115.3 (2 Â d), 114.3 (2 Â d), 55.3 (q). ESI-MS m/z:
276 [M+Na]+, 530 [2M+Na]+.
4.2.14. (E)-3-(6-Flourophenyl)-1-(4-methoxyphenyl)prop-2-en-
1-one (4n)
White solid (1.20 g, 4.68 mmol, 94% yield). Mp 101–103 °C
[lit.23 100 °C]. IR (KBr disk): 3067, 2936, 1654, 1604, 1256,
1225 cmÀ1 1H NMR (200 MHz, CDCl3) d 8.03 (d, J = 8.9 Hz, 2H),
.
7.89 (d, J = 15.8 Hz, 1H), 7.64 (d, J = 15.8 Hz, 1H), 7.65–7.58 (m,
1H), 7.43–7.05 (m, 3H), 6.97 (d, J = 8.9 Hz, 2H), 3.87 (s, 3H). 13C
NMR (50 MHz, CDCl3) d 188.6 (s), 164.2 (s), 163.5 (s), 159.1 (s),
136.6 (d), 131.7 (d), 131.5 (d), 130.9 (2 Â d), 129.8 (s), 124.5 (d),
116.5 (d), 116.0 (d), 113.9 (2 Â d), 55.5 (q). ESI-MS m/z: 257
[M+H]+, 278 [M+Na]+, 534 [2M+Na]+.
4.2.20. (E)-1-(4-Chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-
one (4t)
Pale yellow solid (0.68 g, 2.64 mmol, 53% yield). Mp 155–157 °C
[lit.23 158–160 °C]. IR (KBr disk): 3055, 2916, 1656, 1597,
1086 cmÀ1 1H NMR (200 MHz, CDCl3) d 7.95 (d, J = 8.8 Hz, 2H),
.
7.80 (d, J = 15.6 Hz, 1H), 7.53 (d, J = 8.3 Hz, 2H), 7.45 (d, J = 8.8 Hz,