962 Letters in Drug Design & Discovery, 2011, Vol. 8, No. 10
Kamal et al.
(E)-3-[4-(trifluoromethyl)phenyl]-1-4-[(E)-3-(3,4,5-trimeth-
oxyphenyl)-2propenoyl]piperazino-2-propen-1-one (5c)
Hz),6.73 (d, 1H, J = 15.10 Hz ), 6.70 (s, 2H), 3.87 (s, 6H),
3.85 (s, 3H), 3.75 (brs, 8H); 13C NMR (CDCl3, 150 MHz): ꢀ
165.5, 165.2, 152.3, 143.8, 142.1, 138.8, 134.6, 133.5, 130.2,
129.2, 128.7, 115.8, 115.2, 105.2, 60.7, 56.3, 45.2, 42.1; IR
(KBr) (Umax/cm-1): ꢁ 3483 (br), 2931, 1644, 1603, 1584,
1505, 1488, 1420, 1273, 1217, 1156, 1127, 1072, 1038, 989,
816; ESI-MS: m/z 515 [M]+, HRMS calcd for
C25H27N2O5BrNa [M+Na]+ 537.1001, found 537.0987.
o
1
Yield 83%; White solid; mp 138-142 C; H NMR (300
MHz, CDCl3): ꢀ: 7.70 (d, 1H, J = 15.32 Hz), 7.50 (d, 1H, J =
14.87 ), 7.32 (d, 2H, J = 8.00 Hz), 6.97 (d, 1H, J = 15.32),
6.82 (d, 1H, J = 14.87), 6.73 (s, 2H), 3.92 (s, 6H), 3.87 (s,
3H), 3.78 (brs, 8H); 13C NMR (CDCl3, 150 MHz): ꢀ 165.5,
164.9, 153.3, 143.7, 141.7, 139.7, 138.2, 131.0, 130.3, 127.8,
125.7, 118.8, 115.3, 105.0, 60.8, 56.1, 45.5, 42.1; IR (KBr)
(Umax/cm-1): ꢁ 3433 (br), 2922, 1606, 1584, 1505, 1447,
1418, 1183, 1123, 1067, 1037, 991, 829; ESI-MS: m/z 505
[M+1]+, HRMS calcd for C26H27N2O5F3Na [M+Na]+
527.1769, found 527.1749.
(E)-3-(3,4-Difluorophenyl)-1-4-[(E)-3-(3,4,5-trimethoxy-
phenyl)-2-propenoyl]piperazino-2-propen-1-one (5h)
o
1
Yield 75%; White solid; mp 143-150 C; H NMR (500
MHz, CDCl3): ꢀ: 7.57 (d, 2H, J = 15.60 Hz), 7.37-7.33 (m,
2H), 7.18-7.13 (m, 1H), 6.74 (d, 1H, J = 15.60 Hz),6.70 (s,
2H ), 6.66 (d, 2H, J = 15.60 Hz), 3.89 (s, 6H), 3.84 (s, 3H),
3.74 (brs, 8H); 13C NMR (CDCl3, 150 MHz): ꢀ 165.5, 165.0,
153.3, 143.7, 141.2, 130.3, 124.6, 124.5, 117.8, 117.5, 117.4,
115.9, 115.7, 115.4, 105.0, 60.8, 56.1, 45.5, 42.0; IR (KBr)
(Umax/cm-1): ꢁ 3421 (br), 2937, 1647, 1605, 1586, 1507,
1434, 1419, 1337, 1296, 1277, 1248, 1220, 1126, 1049, 992,
814; ESI-MS: m/z 495 [M+Na]+, HRMS calcd for
C25H26N2O5F2Na [M+Na]+ 495.1707, found 495.1709.
(E)-3-[3-(Trifluoromethoxy)phenyl]-1-4-[(E)-3-(3,4,5-trim-
ethoxyphenyl)-2-propenoyl] piperazin-2-propen-1-one(5d)
o
1
Yield 87%;White solid; mp 260-265 C; H NMR (300
MHz, CDCl3): ꢀ: 7.65 (d, 1H, J = 15.10 Hz), 7.60 (d, 1H, J =
14.32 Hz), 7.43 (s, 2H), 7.37 (s, 1H), 7.27-7.23 (m, 1H), 6.86
(d, 1H, J = 15.10 Hz), 6.74 (s, 3H), 3.90 (s, 6H), 3.87 (s,
3H), 3.78 (brs, 8H); 13C NMR (CDCl3, 150 MHz): ꢀ 165.5,
165.0, 153.3, 149.4, 143.7, 141.7, 139.7, 136.9, 130.3, 130.1,
126.3, 121.8, 119.6, 118.1, 115.4, 104.9, 60.8, 56.0, 45.5,
42.1; IR (KBr) (Umax/cm-1): ꢁ 3448 (br), 2927, 1646, 1607,
1581, 1506, 1456, 1426, 1267, 1211, 1128, 1032, 989, 823;
ESI-MS: m/z 521 [M]+, HRMS calcd for C26H27N2O6F3Na
[M+Na]+ 543.1718, found 543.1732.
(E)-3-(3,4-Dichlorophenyl)-1-4-[(E)-3-(3,4,5-trimethoxy-
phenyl)-2-propenoyl]piperazino-2-propen-1-one (5i )
o
1
Yield 83%; White solid; mp 168-173 C; H NMR (300
MHz, CDCl3): ꢀ: 7.62 (d, 2H, J = 14.87 Hz), 7.42-7.38 (m,
2H), 7.20-7.17 (m, 1H), 6.82 (d, 1H, J = 14.87 Hz),6.68 (s,
2H ), 6.52 (d, 1H, J = 14.87 Hz), 3.89 (s, 6H), 3.82 (s, 3H),
3.71 (brs, 8H); 13C NMR (CDCl3, 150 MHz): ꢀ 165.6, 165.1,
153.2, 143.8, 141.4, 130.2, 124.8, 124.5, 117.8, 117.6, 117.4,
115.9, 115.6, 115.3, 105.2, 60.8, 56.1, 45.5, 42.2; IR (KBr)
(Umax/cm-1): ꢁ 3453 (br), 2936, 1646, 1602, 1581, 1552,
1504, 1455, 1384, 1337, 1272, 1255, 1124, 1028, 990, 922,
819; ESI-MS: m/z 505 [M]+, HRMS calcd for
C25H26N2O5Cl2Na [M+Na]+ 527.1116, found 527.1129.
(E)-3-(4-Fluorophenyl)-1-4-[(E)-3-(3,4,5-trimethoxyphenyl)-
2-propenoyl]piperazino-2-propen-1-one (5e)
o
1
Yield 67%; White solid; mp 172-178 C; H NMR (300
MHz, CDCl3): ꢀ: 7.62 (d, 1H, J = 15.10 Hz), 7.56 (d, 1H, J =
15.10 Hz), 7.50 (dd, 2H, J = 5.28 Hz), 7.06 (2H, t),6.73 (d,
1H, J = 15.10 Hz ), 6.70 (s, 2H), 6.66 (d, 1H, J = 14.80),
3.89 (s, 6H), 3.84 (s, 3H), 3.75 (brs, 8H); 13C NMR (CDCl3,
150 MHz): ꢀ 165.5, 165.4, 153.3, 143.7, 142.3, 139.8, 131.1,
130.4, 129.6, 116.0, 115.4, 105.0, 60.8, 56.1, 45.2, 42.1; IR
(KBr) (Umax/cm-1): ꢁ 3448 (br), 2924, 1608, 1583, 1508,
1446, 1274, 1247, 1126, 1033, 1001, 986, 829; ESI-MS: m/z
455 [M+1]+, HRMS calcd for C25H27N2O5FNa [M+Na]+
477.1801, found 477.1807.
(E)-3-(4-Hydroxy-3-methoxyphenyl)-1-4-[(E)-3-(3,4,5-trim-
ethoxyphenyl)-2-propenoyl] piperazino-2-propen-1-one (5j)
o
1
Yield 87%; White solid; mp 180-185 C; H NMR (300
MHz, CDCl3): ꢀ: 7.65 (d, 1H, J = 15.10 Hz), 7.62 (d, 1H, J =
15.10 Hz), 7.09 (d, 1H, J = 8.30 Hz), 7.00 (s, 1H),6.90 (d,
1H, J = 8.30 Hz ), 6.74 (d, 1H, J = 14.35 Hz), 6.72 (s, 2H),
6.68 (d, 1H, J = 14.35 Hz), 6.19 (brs, 1H), 3.93 (s, 3H), 3.90
(s, 6H), 3.87 (s, 3H), 3.76 (brs, 8H); 13C NMR (CDCl3, 150
MHz): ꢀ 165.9, 165.5, 153.3, 147.7, 146.8, 143.8, 143.7,
130.4, 127.3, 122.0, 115.5, 114.8, 113.5, 109.9, 105.0, 60.8,
56.1, 55.9, 45.5, 42.1; IR (KBr) (Umax/cm-1): ꢁ 3448 (br),
2928, 1639, 1607, 1572, 1506, 1431, 1384, 1337, 1247,
1125, 1032, 989, 822; ESI-MS: m/z 460 [M+1]+, HRMS
calcd for C26H30N2O7Na [M+Na]+ 505.1950, found
505.1975.
(E)-3-(4-Chlorophenyl)-1-4-[(E)-3-(3,4,5-trimethoxyphenyl)-
2-propenoyl]piperazino-2-propen-1-one (5f)
o
1
Yield 84%; White solid; mp 153-158 C; H NMR (300
MHz, CDCl3): ꢀ: 7.60 (d, 1H, J = 15.10 Hz), 7.56 (d, 1H, J =
14.35 Hz), 7.43 (d, 2H, J = 9.06 Hz), 7.32 (d, 2H, J = 8.30
Hz),6.78 (d, 1H, J = 15.10 Hz ), 6.70 (s, 2H), 6.66 (d, 1H, J
= 13.80), 3.89 (s, 6H), 3.84 (s, 3H), 3.74 (brs, 8H); 13C NMR
(CDCl3, 150 MHz): ꢀ 165.6, 165.3, 153.3, 143.7, 142.2,
139.8, 135.6, 133.3, 130.4, 129.0, 128.9, 116.8, 115.4, 105.0,
60.9, 56.1, 45.3, 42.0; IR (KBr) (Umax/cm-1): ꢁ 3429 (br),
2924, 1644, 1604, 1584, 1491, 1446, 1432, 1340, 1275,
1248, 1156, 1124, 1090, 1038, 1010, 991, 980, 820; ESI-
MS: m/z 471 [M]+, HRMS calcd for C25H27N2O5ClNa
[M+Na]+ 493.1506, found 493.1514.
(E)-3-Phenyl-1-(4-(E)-3-[4-(trifluoromethyl)phenyl]-2-pro-
penoylpiperazino)-2-propen-1-one (5k)
o
1
Yield 76%; White solid; mp 182-187 C; H NMR (500
MHz, CDCl3): ꢀ: 7.82 (s, 3H), 7.72 (d, 2H, J = 14.32 Hz),
7.67 (d, 2H, J = 8.23 Hz), 7.62-7.54 (m, 1H),7.42 (d, 1H, J =
14.32 Hz ), 7.39 (s, 3H), 7.32 (d, 1H, , J = 14.28 Hz ), 3.76
(brs, 4H), 3.72 (brs, 4H); 13C NMR (DMSO-d6, 150 MHz): ꢀ
165.4, 153.2, 143.8, 143.4, 139.7, 134.8, 130.6, 129.8, 128.4,
127.6, 116.4, 115.2, 105.3, 45.4, 42.1; IR (KBr) (Umax/cm-
(E)-3-(4-Bromophenyl)-1-4-[(E)-3-(3,4,5-trimethoxyphenyl)-
2-propenoyl]piperazino-2-propen-1-one (5g)
o
1
Yield 79%; White solid; mp 155-160 C; H NMR (300
MHz, CDCl3): ꢀ: 7.59 (d, 2H, J = 15.10 Hz), 7.47 (d, 2H, J =
8.30 Hz), 7.36 (d, 2H, J = 7.55 Hz), 6.82 (d, 1H, J = 15.10