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(d, J = 15.5 Hz, 1H), 7.59 (d, J = 1.9 Hz, 1H), 7.09 (d, J = 8.4 Hz, 1H),
7.01 (d, J = 8.7 Hz, 2H), 3.86 (d, J = 5.6 Hz, 6H), 3.81 (s, J = 3.5 Hz,
3H). 13C NMR (DMSO-d6) d: 187.41, 161.34, 153.22, 148.93,
143.15, 130.91, 130.78, 127.62, 123.27, 119.64, 114.51, 111.06,
110.97, 55.91, 55.76, 55.50. Anal. Calcd for C18H18O4: C, 72.47; H,
6.08. Found: C, 72.12; H, 6.20.
118.25, 114.63, 113.47, 55.57. Anal. Calcd for C20H16O3⁄0.25 H2O:
C, 77.95; H, 5.58. Found: C,77.83; H, 5.37.
4.2.33. (E)-3-(3,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-
2-yl)prop-2-en-1-one (33)
Synthesized from 2-acetyl-1-hydroxynaphthalene and 3,4-
dimethoxybenzaldehyde, yield 79%. 1H NMR (DMSO-d6) d: 14.08
(s, 1H), 8.36 (d, J = 8.2 Hz, 1H), 8.25 (d, J = 9.0 Hz, 1H), 8.14 (d,
J = 15.4 Hz, 1H), 7.94 (d, J = 9.2 Hz, 3H), 7.92 (d, J = 3.9 Hz, 1H),
7.72 (m, 2H), 7.59 (d, J = 8.2, 1H), 7.47 (d, J = 8.9 Hz, 1H), 3.83 (d,
6H). 13C NMR (DMSO-d6) d: 193.60, 158.12, 150.2, 149.90,
144.56, 135.26, 130.93, 129.67, 127.68, 127.35, 126.52, 124.99,
123.25, 122.24, 121.93, 121.12, 120.83, 113.57, 110.67, 55.92,
55.57. Anal. Calcd for C21H18O4: C, 75.43; H, 5.43. Found: C,
75.37; H, 5.51.
4.2.28. (E)-1,3-Bis(3,4-dimethoxyphenyl)prop-2-en-1-one (28)
Synthesized from 3,4-dimethoxyacetophenone and 3,4-dime-
thoxybenzaldehyde, yield 81%. 1H NMR (DMSO-d6) d: 7.80 (d,
J = 15.5 Hz, 1H), 7.66–7.63 (m, 1H), 7.51 (d, J = 2.0 Hz, 1H), 7.41
(d, J = 2.0 Hz, 1H), 7.09 (d, J = 8.5 Hz, 1H), 7.04 (d, J = 2.3 Hz, 1H),
7.02 (d, J = 3.5 Hz, 1H), 6.76 (d, J = 1.0 Hz, 1H), 3.86–3.80 (m,
12H). 13C NMR (DMSO-d6) d: 197.32, 153.17, 153.09, 149.10,
148.61, 143.59, 130.88, 129.90, 123.59, 123.33, 122.74, 119.73,
111.72, 110.93, 110.43, 55.86, 55.81, 55.57, 55.54. Anal. Calcd for
C19H20O5: C, 69.50; H, 6.14. Found: C, 69.34; H, 6.23.
4.2.34. (E)-1-(1-Hydroxynaphthalen-2-yl)-3-(3-
methoxyphenyl)prop-2-en-1-one (34)
4.2.29. (E)-3-(2-Chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-
en-1-one (29)
Synthesized from 2-acetyl-1-hydroxynaphthalene and 3-
methoxybenzaldehyde, yield 67%. 1H NMR (DMSO-d6) d: 14.05 (s,
1H), 8.33 (d, J = 8.7 Hz, 2H), 8.18 (d, J = 15.4 Hz, 1H), 7.93 (dd,
J = 15.4, 7.3 Hz, 3H), 7.86 (d, J = 8.8 Hz, 1H), 7.72 (dddd, J = 14.0,
8.2, 6.9, 1.3 Hz, 2H), 7.63–7.60 (m, 1H), 7.44–7.41 (m, 1H), 3.85
(s, 3H). 13C NMR (DMSO-d6) d: 219.48, 193.80, 163.41, 159.87,
147.20, 145.50, 137.26, 136.00, 130.36, 127.78, 126.34, 125.95,
124.60, 124.36, 123.81, 123.71, 121.45, 117.39, 113.88, 55.54. Anal.
Calcd for C20H16O3⁄0.33 H2O: C, 77.64; H, 5.68. Found: C, 77.59; H,
5.44.
Synthesized from 3,4-dimethoxyacetophenone and 2-chloro-
benzaldehyde, yield 73%. 1H NMR (DMSO-d6) d: 7.99 (d,
J = 4.4 Hz, 1H), 7.65 (dd, J = 8.5, 2.0 Hz, 1H), 7.52 (dd, J = 7.8,
1.7 Hz, 1H), 7.42 (d, J = 2.0 Hz, 1H), 7.36 (dd, J = 7.9, 1.3 Hz, 1H),
7.25–7.22 (m, 1H), 7.18–7.14 (m, 1H), 7.04 (d, J = 8.5 Hz, 2H),
3.83 (s, 3H), 3.79 (s, 3H). 13C NMR (DMSO-d6) d: 196.75, 153.22,
148.65, 141.75, 137.78, 133.08, 129.66, 129.41, 128.37, 127.75,
127.29, 124.94, 122.77, 110.98, 110.47, 55.85, 55.61. Anal. Calcd
for C17H15ClO3⁄0.25 H2O: C, 66.45; H, 5.08. Found: C, 66.67; H,
5.293.
4.2.35. (E)-3-(2-Chlorophenyl)-1-(1-hydroxynaphthalen-2-
yl)prop-2-en-1-one (35)
4.2.30. (E)-3-(4-Chlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-
en-1-one (30)
Synthesized from 2-acetyl-1-hydroxynaphthalene and 2-chlo-
robenzaldehyde, yield 72%. 1H NMR (DMSO-d6) d: 14.81 (s, 1H),
8.39–8.35 (m, 1H), 8.32 (dd, J = 7.5, 2.1 Hz, 1H), 8.29 (d, J = 9.0 Hz,
1H), 8.23 (d, J = 3.0 Hz, 2H), 7.93 (d, J = 8.1 Hz, 1H), 7.73 (ddd,
J = 8.2, 6.9, 1.3 Hz, 1H), 7.63–7.57 (m, 2H), 7.51–7.44 (m, 3H). 13C
NMR (DMSO-d6) d: 193.37, 163.51, 139.61, 137.33, 134.79,
132.53, 132.17, 130.78, 130.23, 129.12, 127.85, 127.78, 126.39,
125.17, 124.55, 123.97, 123.87, 118.52, 113.49. Anal. Calcd for
Synthesized from 3,4-dimethoxyacetophenone and 4-chloro-
benzaldehyde, yield 77%. 1H NMR (DMSO-d6) d: 7.95 (d,
J = 15.6 Hz, 1H), 7.92 (s, J = 1.9 Hz, 1H), 7.90 (dd, J = 8.5, 2.0 Hz,
2H), 7.68 (d, J = 15.6 Hz, 1H), 7.60 (d, J = 2.0 Hz, 1H), 7.51 (d,
J = 8.6 Hz, 2H), 7.10 (d, J = 8.5 Hz, 1H), 3.86 (d, J = 7.8 Hz, 6H). 13C
NMR (DMSO-d6) d: 187.38, 153.50, 148.99, 141.70, 134.99,
133.96, 130.63, 130.63, 130.55, 129.03, 129.03 123.62, 122.90,
111.08, 110.99, 55.95, 55.78. Anal. Calcd for C17H15ClO3: C, 67.44;
H, 4.99. Found: C, 67.19; H, 5.01.
C19H13ClO2: C, 73.91; H, 4.24. Found: C, 74.05; H, 4.19.
4.2.36. (E)-3-(4-Chlorophenyl)-1-(1-hydroxynaphthalen-2-
yl)prop-2-en-1-one (36)
4.2.31. (E)-1-(1-Hydroxynaphthalen-2-yl)-3-phenylprop-2-en-1-
one (31)
Synthesized from 2-acetyl-1-hydroxynaphthalene and 4-chlo-
robenzaldehyde, yield 76%. 1H NMR (DMSO-d6) d: 14.95 (s, 1H),
8.37 (d, J = 8.4 Hz, 1H), 8.31 (d, J = 9.0 Hz, 1H), 8.20 (d, J = 15.5 Hz,
1H), 8.02 (d, J = 8.6 Hz, 2H), 7.95 (d, J = 5.2 Hz, 1H), 7.93 (d,
J = 1.6 Hz, 1H), 7.74–7.70 (m, 1H), 7.64–7.61 (m, 1H), 7.56 (d,
J = 8.5 Hz, 2H), 7.46 (d, J = 8.8 Hz, 1H). 13C NMR (DMSO-d6) d:
193.63, 163.40, 143.92, 137.25, 135.72, 133.57, 131.14, 130.67,
129.14, 127.76, 126.34, 125.17, 124.55, 123.80, 121.96, 118.43,
113.48. Anal. Calcd for C19H13ClO2: C, 73.91; H, 4.24. Found: C,
73.85; H, 4.33.
Synthesized from 2-acetyl-1-hydroxynaphthalene and benzal-
dehyde, yield 88%. 1H NMR (DMSO-d6) d: 15.00 (s, 1H), 8.37 (dd,
J = 8.3, 0.7 Hz, 1H), 8.30 (d, J = 9.0 Hz, 1H), 8.18 (d, J = 15.5 Hz,
1H), 7.97 (dd, J = 6.2, 3.4 Hz, 2H), 7.93 (d, J = 8.3 Hz, 1H), 7.73
(ddd, J = 8.1, 6.9, 1.2 Hz, 1H), 7.60 (ddd, J = 8.2, 6.9, 1.1 Hz, 1H),
7.51–7.48 (m, 3H), 7.46 (d, J = 8.9 Hz, 1H). 13C NMR (DMSO-d6) d:
193.72, 163.37, 145.42, 137.22, 134.59, 131.19, 130.60, 129.45,
129.08, 127.74, 126.30, 125.17, 124.58, 123.78, 121.18, 118.38,
113.47. Anal. Calcd for C19H14O2: C, 83.19; H, 5.14. Found: C,
82.87; H, 5.26.
4.2.37. (E)-3-(3,4-Dichlorophenyl)-1-(1-hydroxynaphthalen-2-
yl)prop-2-en-1-one (37)
4.2.32. (E)-1-(1-Hydroxynaphthalen-2-yl)-3-(4-
methoxyphenyl)prop-2-en-1-one (32)
Synthesized from 2-acetyl-1-hydroxynaphthalene and 3,4-
dichlorobenzaldehyde, yield 64%, mp 161 °C. 1H NMR (DMSO-d6-
d6) d: 14.89 (s, J = 1.5 Hz, 1H), 8.37 (d, J = 1.9 Hz, 1H), 8.33 (d,
J = 9.1 Hz, 1H), 8.27 (d, J = 15.5 Hz, 1H), 7.94 (dd, J = 8.4, 2.3 Hz,
2H), 7.74 (d, J = 8.3 Hz, 2H), 7.71 (ddd, J = 8.2, 5.0, 1.3 Hz, 1H),
7.60 (m, J = 11.3, 8.2, 6.9, 1.2 Hz, 2H), 7.47 (d, J = 8.8 Hz, 1H). 13C
NMR (DMSO-d6) d: 193.57, 163.53, 142.58, 137.36, 135.49,
133.35, 132.09, 131.21, 130.81, 130.63, 129.78, 127.82, 126.43,
125.27, 124.56, 123.87, 123.38, 118.49, 113.54. Anal. Calcd for
Synthesized from 2-acetyl-1-hydroxynaphthalene and 4-
methoxybenzaldehyde, yield 84%. 1H NMR (DMSO-d6) d: 15.18 (s,
1H), 8.36 (d, J = 8.2 Hz, 1H), 8.29 (d, J = 9.0 Hz, 1H), 8.04 (d,
J = 15.4 Hz, 1H), 7.94 (d, J = 9.2 Hz, 3H), 7.92 (d, J = 3.9 Hz, 1H),
7.72 (ddd, J = 8.1, 6.9, 1.3 Hz, 1H), 7.59 (ddd, J = 8.2, 5.0, 1.1 Hz,
1H), 7.45 (d, J = 8.9 Hz, 1H), 7.05 (d, J = 8.8 Hz, 2H), 3.84 (s, 3H).
13C NMR (DMSO-d6) d: 193.59, 163.26, 161.97, 145.58, 137.11,
131.53, 130.45, 127.71, 127.29, 126.22, 125.13, 123.73, 118.42,
C19H12Cl2O2: C, 66.49; H, 3.52. Found: C, 66.23; H, 3.61.