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4ꢀ ꢀA.M. Arasavelli et al.: Anti-cancer activity of novel aryl/heteroaryl chalcone derivatives
(10 mL) the resultant yellow precipitate was filtered and air dried to 121.1, 114.7, 55.2; MS: m/z 446.30 (M+1). Anal. Calcd for C20H15IO2S: C,
give analytically pure compound 5a–l. 53.82; H, 3.39. Found: C, 53.98; H, 3.43.
3-(3-(3-Methoxyphenyl)thiophen-2-yl)-1-phenylprop-2-en-1-one 3-(3-(3-Methoxyphenyl)thiophen-2-yl)-1-(2,4,6-trimethylphenyl)
(5a)ꢀYield 93%; mp 98°C; IR: ν 1658 (Cꢁ=ꢁO), 1597, 1565 (Cꢁ=ꢁC), 1468, prop-2-en-1-one (5g)ꢀYield 93%; mp 120°C; IR: ν 1663 (Cꢁ=ꢁO), 1560
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1261 cm-1; 1H NMR (DMSO-d6): δ 9.23 (s, 1H, Ar-H), 8.81 (d, 1H), 8.41 (d, (Cꢁ=ꢁC), 1462, 1251 cm-1; H NMR (DMSO-d6): δ 7.86 (s, 1H), 7.30 (d, 1H,
1H), 7.89 (d, 1H), 7.88 (d, 2H), 7.57 (m, 2H), 7.47 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH J ꢁ=ꢁ 14.0 Hz, CH of olefin), 6.94 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 6.85
of olefin), 7.32 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 7.03 (3H, m, Ar-H), 3.80 (m, 6H, Ar-H), 3.73 (s, 3H, CH3), 2.22 (s, 9H); 13C NMR (DMSO-d6): δ
(s, 3H, OCH3); 13C NMR (DMSO-d6): δ 187.9, 159.4, 153.2, 149.4, 146.9, 199.3, 159.3, 146.1, 138.0 137.7, 136.7, 135.6, 133.3, 133.2, 130.6, 129.9, 129.7,
136.4, 136.0, 135.8, 134.1, 132.7, 130.6, 129.9, 129.8, 123.8, 121.6, 120.7, 128.0, 126.9, 121.2, 114.2, 113.9, 55.1, 20.6, 18.7; MS: m/z 363.28 (M+1).
114.1, 113.8, 55.2; MS: m/z 322.21 (M+1). Anal. Calcd for C20H16O2S: C, Anal. Calcd for C23H22O2S: C, 76.21; H, 6.12. Found: C, 76.12; H, 6.21.
74.97; H, 5.03. Found: C, 74.89; H, 5.08.
3-(3-(3-methoxyphenyl)thiophen-2-yl)-1-(napthalene-1-yl)prop-
1-(3-Methoxyphenyl)-3-(3-(3-methoxyphenyl)thiophen-2-yl) 2-en-1-one (5h)ꢀYield 94%; mp 119°C; IR: ν 1662 (Cꢁ=ꢁO), 1545 (Cꢁ=ꢁC),
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prop-2-en-1-one (5b)ꢀYield 90%; mp 80°C; IR: ν 1652 (Cꢁ=ꢁO), 1565 1462, 1241 cm-1; H NMR (DMSO-d6): δ 8.12 (s, 1H), 8.01 (d, 1H, Ar-H),
(Cꢁ=ꢁC), 1462, 1265 cm-1; 1H NMR: (DMSO-d6): δ 7.84 (s, 1H), 7.64 (d, 1H), 7.90 (d, 2H, Ar-H), 7.81 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.58 (d, 3H,
7.47 (m, 4H), 7.40 (d, 1H), 7.30 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 7.19 (d, Ar-H), 7.46 (d, 4H, Ar-H), 7.33 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.01 (s,
1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 6.99 (m, 2H), 6.95 (m, 1H), 3.80 (s, 3H, 1H, Ar-H), 3.82 (s, 3H, CH3); 13C NMR (DMSO-d6): δ 196.0, 187.9, 159.4,
CH3), 3.789 (s, 3H, CH3); 13C NMR (DMSO-d6): δ 188.5, 159.5, 159.4, 146.5, 159.0, 153.2, 149.4, 141.4, 138.1, 136.1, 136.0, 132.7, 130.4, 129.8, 129.6,
138.9, 136.1,135.8, 134.2, 130.6, 129.9, 129.9, 129.3, 121.5, 121.1, 120.8, 129.2, 127.2, 121.5, 120.7, 114.1, 113.6, 55.2, 45.8; MS: m/z 371.15 (M+1).
119.1, 114.6, 113.7, 112.8, 55.2, 39.5; MS: m/z 351.10 (M+1). Anal. Calcd Anal. Calcd for C24H18O2S: C, 77.81; H, 4.90. Found: C, 78.31; H, 4.94.
for C21H18O3S: C, 71.98; H, 5.18. Found: C, 72.01; H, 5.21.
3-(3-(3-methoxyphenyl)thiophen-2-yl)-1-(napthalene-2-yl)-prop-
1-(4-methoxyphenyl)-3-(3-(3-methoxyphenyl)thiophen-2-yl) 2-en-1-one (5i)ꢀYield 94%; mp 119°C; IR: ν 1662 (Cꢁ=ꢁO), 1545 (Cꢁ=ꢁC),
prop-2-en-1-one (5c)ꢀYield 92%; mp 85°C; IR: ν 1658 (Cꢁ=ꢁO), 1565 1462, 1241 cm-1; 1H NMR (DMSO-d6): δ 8.07 (s, 1H), 8.02 (d, 1H, Ar-H),
(Cꢁ=ꢁC), 1480, 1260 cm-1; 1H NMR (DMSO-d6): δ 8.29 (m, 2H), 7.85 (d, 1H), 7.94 (d, 2H, Ar-H), 7.83 (d,2H), 7.54 (d, 3H, Ar-H), 7.42 (d, 3H, Ar-H), 7.32
7.50 (m, 4H), 7.45 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 7.21 (d, 1H, J ꢁ=ꢁ 14.5 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.01 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin),
Hz, CH of olefin), 6.98 (m, 3H), 3.80 (s, 3H, OCH3), 3.79 (s, 3H, OCH3); 3.82 (s, 3H, CH3); 13C NMR (DMSO-d6): δ 197.0, 187.5, 159.4, 159.4, 159.1,
13C NMR (DMSO-d6): δ 188.4, 159.6, 159.3, 146.5, 138.8, 136.1, 135.8, 146.8, 141.4, 139.3, 138.1, 136.4, 136.0, 134.2, 130.8, 130.6, 130.6, 129.9,
134.3, 130.6, 129.9, 129.9, 129.3, 121.5, 121.1, 120.8, 119.1, 114.6, 113.7, 129.6, 129.2, 127.7, 127.1, 120.9, 114.6, 113.7, 95.2, 55.1, 54.9, 45.8. MS: m/z
112.8, 79.1, 55.3, 55.1; MS: m/z 351.20 (M+1). Anal. Calcd for C21H18O3S: 371.15, 372.17 (M+1). Anal. Calcd for C24H18O2S: C, 77.81; H, 4.90. Found:
C, 71.98; H, 5.18. Found: C, 71.81; H, 5.16.
C, 77.62; H, 4.87.
1-(4-Bromophenyl)-3-(3-(3-methoxyphenyl)thiophen-2-yl)prop- 3-(3-(3-methoxyphenyl)thiophen-2-yl)-1-(pyridin-2-yl)-prop-
2-en-1-one (5d)ꢀYield 92%; mp 136°C; IR: (KBr, cm-1) ν: 1652 (Cꢁ=ꢁO), 2-en-1-one (5j)ꢀYield 92%; mp 158°C; IR: ν 1675 (Cꢁ=ꢁO), 1576, 1525
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1567 (Cꢁ=ꢁC), 1472, 1241 cm-1; 1H NMR (DMSO-d6): δ 8.013 (d, 2H), 7.86 (d, (Cꢁ=ꢁC), 1482, 1224, 970 cm-1; H NMR (DMSO-d6): δ 8.81 (d, 1H, Ar-H),
2H), 7.75 (d, 2H), 7.54 (1H, s), 7.50 (1H, s), 7.44 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of 8.04 (m, 3H, Ar-H), 7.94 (s, 1H), 7.85 (d, 1H, J ꢁ=ꢁ 14.3 Hz, CH of olefin),
olefin), 7.33 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 6.9 (m, 2H), 3.82 (s, 3H, 7.68 (d, 1H, J ꢁ=ꢁ 14.3 Hz, CH of olefin), 7.46 (s, 1H), 7.34 (d, 1H, Ar-H),
CH3); 13C NMR (DMSO-d6): δ 187.7, 159.4, 146.7, 136.4, 136.2, 136.0, 134.2, 7.034 (m, 3H, Ar-H), 3.83 (s, 3H, CH3); 13C NMR (DMSO-d6): δ 187.9,
131.8, 130.6, 130.4, 129.9, 129.2, 127.2, 121.6, 120.5, 114.7, 113.7, 112.5, 55.2, 159.4, 153.1, 149.1, 146.7, 137.7, 136.0, 135.5, 134.5, 130.8, 129.9, 129.4,
39.9. MS: m/z 399.18, 401.16 (M+2). Anal. Calcd for C20H15BrO2S: C, 127.6, 122.3, 121.5, 119.8, 114.6, 113.8, 55.2; MS: m/z 322.0 (M+1). Anal.
60.16; H, 3.79. Found: C, 60.24; H, 3.82.
Calcd for C19H15NO2S: C, 71.00; H, 4.70; N, 4.36. Found: C, 71.12; H,
4.65; N, 4.28.
1-(4-Chlorophenyl)-3-[3-(3-methoxyphenyl)thiophen-2-yl]prop-
2-en-1-one (5e)ꢀYield 94%; mp 123°C; IR: ν 1685 (Cꢁ=ꢁO), 1557 (Cꢁ=ꢁC), 3-(3-(3-methoxyphenyl)thiophen-2-yl)-1-(pyridin-3-yl)prop-2-
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1482, 1261 cm-1; H NMR (DMSO-d6): δ 8.09 (d, 2H), 7.87 (d, 2H), 7.61 en-1-one (5k)ꢀYield 92%; mp 140°C; IR: ν 1682 (Cꢁ=ꢁO), 1567 (Cꢁ=ꢁC),
(m, 2H), 7.55 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.51 (m, 1H), 7.44 (d, 1482, 1261, 975 cm-1; H NMR (DMSO-d6): δ 9.23 (S, 1H Py-H), 8.80 (d,
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1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.33 (3H, m), 3.8 (s, 3H, OCH3); 13C NMR 1H, Py-H), 8.40 (d, 1H, Py-H), 7.90 (2H, m), 7.65 (m, 2H), 7.43-7.09 (m,
(DMSO-d6): δ 187.5, 159.4, 146.7, 138.0, 136.1, 136.0, 136.0,134.2, 130.6, 3H), 7.42 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.30 (d, 1H, J ꢁ=ꢁ 14.0 Hz,
130.2, 129.9, 129.5, 128.8, 121.5, 120.6, 114.6, 113.7, 55.2, 39.9; MS: m/z CH of olefin), 3.8 (s, 3H, OCH3); 13C NMR (DMSO-d6): δ 187.9, 159.4,
355.11 (M+1). Anal. Calcd for C20H15ClO2S: C, 67.69; H, 4.28. Found: C, 153.1, 149.1, 146.7, 137.7, 136.0, 135.5, 134.6, 130.8, 129.4, 127.6, 122.3,
67.62; H, 4.31.
121.5, 119.8, 114.6, 113.8, 55.2; MS: m/z 322.0 (M+1). Anal. Calcd for
C19H15NO2S: C, 71.00; H, 4.70; N, 4.36. Found: C, 71.15; H, 4.61; N, 4.30.
1-(4-Iodophenyl)-3-(3-(3-methoxyphenyl)thiophen-2-yl)prop-
2-en-1-one (5f)ꢀYield 95%; mp 97°C; IR: ν 1662 (Cꢁ=ꢁO), 1557 (Cꢁ=ꢁC), 3-(3-(3-Methoxyphenyl)thiophen-2-yl)-1-(thiophen-2-yl)-prop-2-
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1482, 1261 cm-1; H NMR (DMSO-d6): δ 8.86 (s, 1H), 8.21 (d, 1H), 8.05 en-1-one (5l)ꢀYield 94%; mp 129°C; IR: ν 1642 (Cꢁ=ꢁO), 1546 (Cꢁ=ꢁC),
(m, 2H), 7.97 (m, 1H), 7.88 (s, 1H), 7.77 (m, 2H), 7.72 (d, 1H, J ꢁ=ꢁ 14.0 Hz, 1462, 1261 cm-1; 1H NMR (DMSO-d6): δ 8.25 (s, 1H), 8.24 (d, 1H, Ar-H),
CH of olefin), 7.70 (d, 1H, J ꢁ=ꢁ 14.0 Hz, CH of olefin), 7.68 (m, 2H), 3.82 7.85 (d, 2H), 7.53 (m, 2H, Ar-H), 7.49 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin),
(s, 3H); 13C NMR (DMSO-d6): δ 188.4, 159.4, 146.5, 136.1, 135.7, 134.5, 7.49 (d, 1H, J ꢁ=ꢁ 14.5 Hz, CH of olefin), 7.43 (m, 3H), 3.82 (s, 3H, OCH3);
134.4, 132.2, 130.6, 130.1, 129.9, 129.6, 129.2, 128.4, 127.6, 124.0, 121.6, 13C NMR (DMSO-d6): δ 180.9, 159.4, 146.5, 145.1, 136.1, 135.4, 134.8,
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