Arch. Pharm. Chem. Life Sci. 2011, 344, 689–695
Synthesis, Antibacterial Evaluation of Chalcone Analogues
693
(3H, m, H-3’,2,6), 7.35 (1H, d, J ¼ 15.3 Hz, H-a), 7.25–7.30
(1H, m, H-5), 7.03 (1H, d, J ¼ 7.2 Hz, H-4), 6.67 (1H, d,
J ¼ 3.0 Hz, H-5’), 6.48 (1H, t, J ¼ 1.5 Hz, H-4’); IR (KBr,
(E)-3-(Furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
F3
Yield: 97%; m.p.: 76–788C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 8.05 (2H, d, J ¼ 8.4 Hz, H-2,6), 7.57 (1H, d, J ¼ 15.6 Hz, H-b),
7.53–7.62 (1H, m, H-3’), 7.44 (1H, d, J ¼ 8.4 Hz, H-3,5), 7.38
(1H, d, J ¼ 15.6 Hz, H-a), 6.72 (1H, d, J ¼ 3.0 Hz, H-5’),
6.53 (1H, t, J ¼ 1.5 Hz, H-4’), 3.90 (3H, s, CH3); IR (KBr,
nmax cmꢁ1
)
1639; ESI-MS m/z: 215 (M þ 1); Anal. calcd.
for C13H10O3: C, 72.89; H, 4.71. Found: C, 72.94; H, 4.76.
(E)-3-(Furan-2-yl)-1-(3-methoxyphenyl)prop-2-en-1-one
nmax cmꢁ1
)
1629; ESI-MS m/z: 233 (M þ 1); Anal. calcd.
F10
Yield: 93%; m.p.: 39–418C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.62 (1H, d, J ¼ 15.3 Hz, H-b), 7.53–7.60 (3H, m, H-3’,2,6),
7.40–7.46 (1H, m, H-5), 7.38 (1H, d, J ¼ 15.3 Hz, H-a), 7.13 (1H,
d, J ¼ 7.2 Hz, H-4), 6.72 (1H, d, J ¼ 3.0 Hz, H-5’), 6.52 (1H,
for C13H9O2: C, 73.67; H, 5.30. Found: C, 73.76; H, 5.36.
(E)-1-(4-Fluorophenyl)-3-(furan-2-yl)prop-2-en-1-one F4
Yield: 95%; m.p.: 63–658C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 8.06 (2H, dd, J ¼ 8.4 Hz, H-2,6), 7.59 (1H, d, J ¼ 15.3 Hz, H-b),
7.47–7.55 (1H, m, H-3’), 7.38 (1H, d, J ¼ 15.3 Hz, H-a), 7.18 (1H,
dd, J ¼ 8.4 Hz, H-3,5), 6.74 (1H, d, J ¼ 3.0 Hz, H-5’), 6.54 (1H,
t, J ¼ 1.5 Hz, H-4’); IR (KBr, nmax cmꢁ1) 1641; ESI-MS m/z: 217
(M þ 1); Anal. calcd. for C13H9FO2: C, 72.22; H, 4.20. Found: C,
72.18; H, 4.33.
t, J ¼ 1.5 Hz, H-4’), 3.88 (3H, s, OCH3); IR (KBr, nmax cmꢁ1
)
1637; ESI-MS m/z: 229 (M þ 1); Anal. calcd. for C14H12O3: C,
73.67; H, 5.30. Found: C, 73.74; H, 5.33.
(E)-3-(Furan-2-yl)-1-(2, 4-dimethylphenyl)prop-2-en-1-one
F11
Yield: 95%; m.p.: 58–608C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.51 (1H,d, J ¼ 1.5 Hz, H-3’), 7.46 (1H, d, J ¼ 8.1 Hz, H-6),
7.27 (1H, d, J ¼ 15.3 Hz, H-b), 7.09–7.11 (2H, m, H-3,5), 7.06
(1H, d, J ¼ 15.3 Hz, H-a), 6.65 (1H, d, J ¼ 3.0 Hz, H-5’), 6.50
(1H, t, J ¼ 1.5 Hz, H-4’), 2.45 (3H, s, CH3), 2.37 (3H, s, CH3); IR
(KBr, nmax cmꢁ1) 1632; ESI-MS m/z: 227 (M þ 1); Anal. calcd.
for C15H14O2: C, 79.62; H, 6.24. Found: C, 79.68; H, 6.31.
(E)-3-(Furan-2-yl)-1-p-tolylprop-2-en-1-one F5
Yield: 98%; m.p.: 62–648C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.94 (2H, d, J ¼ 8.4 Hz, H-2,6), 7.62 (1H, d, J ¼ 15.3 Hz, H-b),
7.53–7.57 (1H, m, H-3’), 7.44 (1H, d, J ¼ 15.3 Hz, H-a), 7.28 (1H,
d, J ¼ 8.4 Hz, H-3,5), 6.70 (1H, d, J ¼ 3.0 Hz, H-5’), 6.52 (1H,
t, J ¼ 1.5 Hz, H-4’), 2.43 (1H, s, CH3); IR (KBr, nmax cmꢁ1) 1635;
ESI-MS m/z: 213 (M þ 1); Anal. calcd. for C14H12O2: C, 79.22;
H, 5.70. Found: C, 79.27; H, 5.73.
(E)-1-(2, 4-Dichlorophenyl)-3-(furan-2-yl)prop-2-en-1-one
F12
Yield: 95%; m.p.: 79–818C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.55 (1H,s, H-3), 7.47 (1H, d, J ¼ 1.8 Hz, H-3’), 7.43 (1H,
d, J ¼ 8.4 Hz, H-6), 7.33 (1H, m, H-5), 7.24 (1H, d, J ¼ 15.3 Hz,
H-b), 6.99 (1H, d, J ¼ 15.3 Hz, H-a), 6.72 (1H, d, J ¼ 3.0 Hz, H-5’),
6.52 (1H, t, J ¼ 1.5 Hz, H-4’); IR (KBr, nmax cmꢁ1) 1621; ESI-MS
m/z: 268 (M þ 1); Anal. calcd. for C13H8Cl2O2: C, 58.46; H, 3.02.
Found: C, 58.55; H, 3.07.
(E)-3-(Furan-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one F6
Yield: 98%; m.p.: 148–1508C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.94 (2H, d, J ¼ 8.4 Hz, H-3,5), 7.28 (1H, d, J ¼ 8.4 Hz, H-2,6),
7.67 (1H, d, J ¼ 15.3 Hz, H-b), 7.62–7.66 (1H, m, H-3’), 7.38 (1H,
d, J ¼ 15.3 Hz, H-a), 6.81 (1H, d, J ¼ 3.0 Hz, H-5’), 6.56 (1H,
t, J ¼ 1.5 Hz, H-4’); IR (KBr, nmax cmꢁ1) 1625; ESI-MS m/z: 244
(M þ 1); Anal. calcd. for C13H9NO2: C, 64.20; H, 3.73; N, 5.76.
Found: C, 64.27; H, 3.79; N, 5.66.
(E)-3-(Furan-2-yl)-1-(2, 4-dihydroxyphenyl)prop-2-en-1-
(E)-1-(4-Bromophenyl)-3-(furan-2-yl)prop-2-en-1-one F7
Yield: 98%; m.p.: 80–828C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 7.89 (2H, d, J ¼ 8.4 Hz, H-3,5), 7.62 (1H, d, J ¼ 8.4 Hz, H-2,6),
7.58 (1H, d, J ¼ 15.3 Hz, H-b), 7.54–7.57 (1H, m, H-3’), 7.37
(1H, d, J ¼ 15.3 Hz, H-a), 6.74 (1H, d, J ¼ 3.0 Hz, H-5’), 6.53
(1H, t, J ¼ 1.5 Hz, H-4’); IR (KBr, nmax cmꢁ1) 1628; ESI-MS
m/z: 278 (M þ 1); Anal. calcd. for C13H9BrO2: C, 56.34; H, 3.27.
Found: C, 56.42; H, 3.31.
one F13
Yield: 75%; m.p.: 69–718C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 13.43 (1H, s, 2-OH), 7.83 (1H,d, J ¼ 8.4 Hz, H-6), 7.63
(1H, d, J ¼ 15.6 Hz, H-b), 7.45–7.50 (2H, m, H-3,5), 7.45
(1H, d, J ¼ 15.3 Hz, H-a), 6.75 (1H, d, J ¼ 3.0 Hz, H-5’), 6.55 (1H,
d, J ¼ 3.0 Hz, H-3’), 6.45 (1H, t, J ¼ 1.5 Hz, H-4’), 6.43 (1H, s, 4-OH);
IR (KBr, nmax cmꢁ1) 1648; ESI-MS m/z: 231 (M þ 1); Anal. calcd.
for C13H10O4: C, 67.82; H, 4.38. Found: C, 67.89; H, 4.37.
(E)-3-(Furan-2-yl)-1-(3-hydroxyphenyl)prop-2-en-1-one
(E)-3-(Furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one
F8
F14
Yield: 98%; m.p.: 44–468C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 8.00 (1H, s, H-2), 7.88 (1H, d, J ¼ 8.4 Hz, H-6), 7.58
(1H, d, J ¼ 15.3 Hz, H-b), 7.43–7.55 (3H, m, H-3’,4,5), 7.36 (1H,
d, J ¼ 15.3 Hz, H-a), 6.74 (1H, d, J ¼ 3.0 Hz, H-5’), 6.53 (1H,
t, J ¼ 1.5 Hz, H-4’); IR (KBr, nmax cmꢁ1) 1639; ESI-MS m/z: 233
(M þ 1); Anal. calcd. for C13H9O2: C, 67.11; H, 3.90. Found: C,
67.17; H, 3.98.
Yield: 96%; m.p.: 103–1058C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 12.90 (1H, s, 2-OH), 7.93 (1H, d, J ¼ 6), 7.68 (1H, d, J ¼ 15.3 Hz,
H-b), 7.55 (1H, d, J ¼ 15.3 Hz, H-a), 7.47–7.60 (2H, m, H-4,3’), 7.03
(1H, d, J ¼ 8.4 Hz, H-3), 6.96 (1H, t, J ¼ 7.5 Hz, H-5), 6.80 (1H, d,
J ¼ 3.0 Hz, H-5’), 6.56 (1H, t, J ¼ 1.5 Hz); IR (KBr, nmax cmꢁ1) 1627;
ESI-MS m/z: 215 (M þ 1); Anal. calcd. for C14H12O3: C, 72.89;
H, 4.71. Found: C, 73.94; H, 4.63.
(E)-3-(Furan-2-yl)-1-(3-chlorophenyl)prop-2-en-1-one F9
Yield: 93%; m.p.: 71–738C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 8.85 (1H, s, OH), 7.49 (1H, d, J ¼ 15.3 Hz, H-b), 7.40–7.47
(E)-3-(2-Chloroquinolin-3-yl)-1-phenylprop-2-en-1-one Q1
Yield: 83%; m.p.: 138–1408C; 1H-NMR (CDCl3, 300 MHz, d, ppm)
d: 8.49 (1H, s, H-8’), 8.18 (1H, d, J ¼ 15.6 Hz, H-b), 8.02–8.08
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