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H, –OH), 12.41 (s, H, –OH); IR (KBr) cm-1: 3328 (OH),
2-Chloro-20,40,60-trihydroxychalcone (3e)
1649 (C=O); MS m/z 325 (M ? 1).
MP 160–162°C; yield = 63%; 1H-NMR (DMSO-d6,
300 MHz): d 5.88–7.84 (m, 6H, Ar–H), 7.94 (d, 1H,
J = 15.6 Hz, Ha), 8.16 (d, 1H, J = 15.6 Hz, Hb), 10.57 (s,
H, –OH), 12.45 (s, H, –OH); IR (KBr) cm-1: 3322 (OH),
1644 (C=O); MS m/z 291 (M ? 1).
4-Methyl-20,40,60-trihydroxychalcone (3l)
MP 117–119°C; yield = 60%; 1H-NMR (DMSO-d6,
300 MHz): d 2.35 (s, 3H, CH3), 5.90–7.44 (m, 6H, Ar–H),
7.67 (d, 1H, J = 15.7 Hz, Ha), 8.09 (d, 1H, J = 15.7 Hz,
Hb), 10.46 (s, H, –OH), 12.50 (s, H, –OH); IR (KBr) cm-1
:
3-Chloro-20,40,60-trihydroxychalcone (3f)
3330 (OH), 1646 (C=O); MS m/z 271 (M ? 1).
MP 178–180°C; yield = 72%; 1H-NMR (DMSO-d6,
300 MHz): d 5.92–7.74 (m, 6H, Ar–H), 7.63 (d, 1H,
J = 15.7 Hz, Ha), 8.13 (d, 1H, J = 15.7 Hz, Hb), 10.53 (s,
H, –OH), 12.45 (s, H, –OH); IR (KBr) cm-1: 3327 (OH),
1647 (C=O); MS m/z 291 (M ? 1).
3,4-Dimethyl-20,40,60-trihydroxychalcone (3m)
MP 156–158°C; yield = 68%; 1H-NMR (DMSO-d6,
300 MHz): d 2.23 (s, 6H, (CH3)2), 5.85–7.44 (m, 5H, Ar–
H), 7.64 (d, 1H, J = 15.7 Hz, Ha), 8.09 (d, 1H,
J = 15.7 Hz, Hb), 10.44 (s, H, –OH), 12.50 (s, H, –OH);
IR (KBr) cm-1: 3329 (OH), 1645 (C=O); MS m/z 285
(M ? 1).
4-Chloro-20,40,60-trihydroxychalcone (3g)
MP 175–177°C; yield = 78%; 1H-NMR (DMSO-d6,
300 MHz): d 5.86–7.71 (m, 6H, Ar–H), 7.67 (d, 1H,
J = 15.1 Hz, Ha), 8.11 (d, 1H, J = 15.7 Hz, Hb), 10.51 (s,
H, –OH), 12.46 (s, H, –OH); IR (KBr) cm-1: 3328 (OH),
1649 (C=O); MS m/z 291 (M ? 1).
4-Methoxyl-20,40,60-trihydroxychalcone (3n)
MP 107–109°C; yield = 68%; 1H-NMR (DMSO-d6,
300 MHz):d 3.82 (s, 3H, OCH3), 5.85–7.65 (m, 6H, Ar–H),
7.69 (d, 1H, J = 15.8 Hz, Ha), 8.03 (d, 1H, J = 15.6 Hz,
2-Bromo-20,40,60-trihydroxychalcone (3h)
Hb), 10.42 (s, H, –OH), 12.52 (s, H, –OH); IR (KBr) cm-1
:
MP 186–188°C; yield = 53%; 1H-NMR (DMSO-d6,
300 MHz): d 5.87–7.82 (m, 6H, Ar–H), 7.90 (d, 1H,
J = 15.5 Hz, Ha), 8.10 (d, 1H, J = 15.5 Hz, Hb), 10.55 (s,
H, –OH), 12.43 (s, H, –OH); IR (KBr) cm-1: 3328 (OH),
1640 (C=O); MS m/z 334 (M ? 1).
3327 (OH), 1646 (C=O); MS m/z 287 (M ? 1).
3,4-Dimethoxy-20,40,60-trihydroxychalcone (3o)
MP 112–114°C; yield = 68%; 1H-NMR (DMSO-d6,
300 MHz): d 3.77, 3.82 (each s, 3H, OCH3-3,4), 5.90–7.65
(m, 5H, Ar–H), 7.64 (d, 1H, J = 15.7 Hz, Ha), 8.09 (d, 1H,
J = 15.7 Hz, Hb), 10.41 (s, H, –OH), 12.53 (s, H, –OH);
IR (KBr) cm-1: 3327 (OH), 1646 (C=O); MS m/z 317
(M ? 1).
3-Bromo-20,40,60-trihydroxychalcone (3i)
MP 182–184°C; yield = 65%; 1H-NMR (DMSO-d6,
300 MHz): d 5.86–7.88 (m, 6H, Ar–H), 7.63 (d, 1H,
J = 15.7 Hz, Ha), 8.12 (d, 1H, J = 15.7 Hz, Hb), 10.52 (s,
H, –OH), 12.45 (s, H, –OH); IR (KBr) cm-1: 3335 (OH),
1651 (C=O); MS m/z 334 (M ? 1).
3,4,20,40,60-Pentahydroxychalcone (3p)
MP 202–204°C; yield = 68%; 1H-NMR (DMSO-d6,
300 MHz): d 5.89–7.41 (m, 5H, Ar–H), 7.65 (d, 1H,
J = 15.6 Hz, Ha), 8.06 (d, 1H, J = 15.7 Hz, Hb), 9.67 (s,
H, –OH), 10.37 (s, H, –OH), 12.12 (s, H, –OH), 12.51
(s, H, –OH); IR (KBr) cm-1: 3328 (OH), 1647 (C=O); MS
m/z 289 (M ? 1).
4-Bromo-20,40,60-trihydroxychalcone (3j)
MP 192–194°C; yield = 69%; 1H-NMR (DMSO-d6,
300 MHz): d 5.86–7.65 (m, 6H, Ar–H), 7.65 (d, 1H,
J = 15.7 Hz, Ha), 8.12 (d, 1H, J = 15.7 Hz, Hb), 10.51 (s,
H, –OH), 12.46 (s, H, –OH); IR (KBr) cm-1: 3322 (OH),
1647 (C=O); MS m/z 334 (M ? 1).
3-Methoxy-4,20,40,60-tetrahydroxychalcone (3q)
2,4-Dichloro-20,40,60-trihydroxychalcone (3k)
MP 188–190°C; yield = 68%; 1H-NMR (DMSO-d6,
300 MHz): d 3.83 (s, 3H, OCH3), 5.89–7.27 (m, 5H, Ar–
H), 7.65 (d, 1H, J = 15.5 Hz, Ha), 7.99 (d, 1H,
J = 15.7 Hz, Hb), 10.38 (s, H, –OH), 10.78 (s, H, –OH);
MP 179–181°C; yield = 71%; 1H-NMR (DMSO-d6,
300 MHz): d 5.88–7.76 (m, 5H, Ar–H), 7.86 (d, 1H,
J = 15.7 Hz, Ha), 8.14 (d, 1H, J = 15.6 Hz, Hb), 10.57 (s,
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