B. P. Bandgar et al. / Bioorg. Med. Chem. 20 (2012) 5649–5657
5655
1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 15.6 Hz, CH@CH), 7.94–8.15 (m,
6H, ArH and CH@CH), 8.23 (d, 1H, J = 8.0 Hz, ArH), 8.43 (s, 1H, ArH),
8.75 (s, 1H, ArH), 10.54 (s, 1H, NH); m/z = 449.20 (m+1).
1H NMR (400 MHz, DMSO-d6, d in ppm): 3.93 (s, 3H, NCH3), 7.29
(t, 1H, J = 7.6 Hz, ArH), 7.52 (t, 1H, J = 8.0 Hz, ArH), 7.56–7.65 (m,
3H, ArH), 7.70 (d, 2H, J = 8.4 Hz, ArH), 7.92 (d, 1H, J = 16 Hz,
CH@CH), 7.95–8.06 (m, 4H, ArH and CH@CH), 8.08 (s, 1H, ArH),
8.14 (d, 1H, J = 8.4 Hz, ArH), 8.23 (d, 1H, J = 7.6 Hz, ArH), 8.44 (s,
1H, ArH), 8.75 (s, 1H, ArH), 10.59 (s, 1H, NH); m/z = 499.25 (m+1).
4.3.8. 3-Bromo-N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-
phenyl}-benzamide (7h)
Yield 81%; Mp: 119–122 °C; IR (KBr, cmÀ1): 3297, 2926, 1654,
1560, 1464, 1433, 1205, 1105, 917, 805, 738; 1H NMR (400 MHz,
DMSO-d6, d in ppm): 3.94 (s, 3H, NCH3), 7.29 (t, 1H, J = 7.6 Hz,
ArH), 7.52 (t, 1H, J = 8.0 Hz, ArH), 7.60 (t, 2H, J = 7.6 Hz, ArH),
7.64 (d, 1H, J = 8.0 Hz, ArH), 7.70 (d, 2H, J = 8.8 Hz, ArH), 7.90 (d,
1H, J = 15.6 Hz, CH@CH), 7.95–8.06 (m, 4H, ArH and CH@CH),
8.10 (s, 1H, ArH), 8.14 (d, 1H, J = 8.0 Hz, ArH), 8.23 (d, 1H,
J = 8.0 Hz, ArH), 8.44 (s, 1H, ArH), 8.76 (s, 1H, ArH), 10.59 (s, 1H,
NH); m/z = 509 (m+), 511.20 (m+2).
4.3.14. Furan-2-carboxylic acid {3-[3-(9-methyl-9H-carbazol-3-
yl)-acryloyl]-phenyl}-amide (7n)
Yield 63%; Mp: 120–122 °C IR (KBr, cmÀ1): 3306, 2923, 1656,
1592, 1467, 1319, 1204, 1105, 1108, 759, 589; 1H NMR
(400 MHz, DMSO-d6, d in ppm): 3.93 (s, 3H, NCH3), 6.73 (m, 1H,
ArH of furan), 7.28 (t, 1H, J = 8.0 Hz, ArH), 7.40 (m, 1H, ArH of fur-
an), 7.52 (t, 1H, J = 8.0 Hz, ArH), 7.59 (t, 1H, J = 8.4 Hz), 7.64 (d, 1H,
J = 15.2 Hz, CH@CH), 7.69 (d, 1H, J = 15.2 Hz, CH@CH), 7.82–8.06
(m, 5H, ArH and ArH of furan), 8.10 (d, 1H, J = 8.0 Hz, ArH), 8.22
(d, 1H, J = 8.0 Hz, ArH), 8.43 (s, 1H, ArH), 8.75 (s, 1H, ArH), 10.41
(s, 1H, NH); m/z = 421.30 (m+1).
4.3.9. 2-Methyl-N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-
phenyl}-benzamide (7i)
Yield 80%; Mp: 150–152 °C; IR (KBr, cmÀ1): 3294, 2931, 2845,
1655, 1590, 1460, 1318, 1257, 1205, 1106, 920, 806; 1H NMR
(400 MHz, DMSO-d6, d in ppm): 2.40 (s, 3H, CH3), 3.92 (s, 3H,
NCH3), 7.28 (t, 1H, J = 8.0 Hz, ArH), 7.40–7.61 (m, 4H, ArH), 7.64
(d, 1H, J = 8.0 Hz, ArH), 7.70 (d, 1H, J = 15.2 Hz, CH@CH), 7.80–
8.06 (m, 6H, ArH and CH@CH), 8.14 (d, 1H, J = 8.0 Hz, ArH), 8.23
(d, 1H, J = 8.0 Hz, ArH), 8.43 (s, 1H, ArH), 8.74 (s, 1H, ArH), 10.45
(s, 1H, NH); m/z = 445.30 (m+1).
4.3.15. Thiophene-2-carboxylic acid {3-[3-(9-methyl-9H-
carbazol-3-yl)-acryloyl]-phenyl}-amide (7o)
Yield 60%; Mp: 90–93 °C; IR (KBr, cmÀ1): 3315, 2924, 1650,
1590, 1432, 1317, 1205, 1105, 738; 1H NMR (400 MHz, DMSO-d6,
d in ppm): 3.93 (s, 3H, NCH3), 7.28 (t, 1H, J = 8.0 Hz, ArH), 7.49–
7.73 (m, 5H, ArH), 7.86–8.13 (m, 7H, ArH), 8.24 (d, 1H, J = 8.0 Hz,
ArH), 8.38 (s, 1H, ArH), 8.76 (s, 1H, ArH), 10.47 (s, 1H, NH); m/
z = 437.15 (m+1).
4.3.10. 3-Methyl-N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-
phenyl}-benzamide (7j)
4.3.16. N-{3-[3-(9-Methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-
3-phenyl-acrylamide (7p)
Yield 77%; Mp: 155–160 °C; IR (KBr, cmÀ1): 3305, 2931, 2845,
1655, 1590, 1460, 1318, 1257, 1205, 1106, 920, 806, 738; 1H
NMR (400 MHz, DMSO-d6, d in ppm): 2.41 (s, 3H, CH3), 3.92 (s,
3H, NCH3), 7.27 (t, 1H, J = 8.0 Hz, ArH), 7.42 (s, 1H, ArH), 7.52 (t,
1H, J = 8.0, ArH), 7.59 (t, 1H, J = 8.4 Hz, ArH), 7.64 (d, 1H,
J = 15.2 Hz, CH@CH), 7.70 (d, 1H, J = 15.2 Hz, CH@CH), 7.79–8.05
(m, 7H, ArH), 8.14 (d, 1H, J = 8.0 Hz, ArH), 8.24 (d, 1H, J = 8.0 Hz,
ArH), 8.43 (s, 1H, ArH), 8.74 (s, 1H, ArH), 10.45 (s, 1H, NH); m/
z = 445.30 (m+1).
Yield 65%; Mp: 162–165 °C; IR (KBr, cmÀ1): 3315, 2926, 1657,
1591, 1463,1257, 1106, 1013, 849, 760, 686; 1H NMR (400 MHz,
DMSO-d6, d in ppm): 3.91 (s, 3H, NCH3), 6.84 (d, 1H, J = 16.0 Hz,
CH@CH), 7.28 (t, 1H, J = and 8.0 Hz, ArH), 7.40–7.72 (m, 5H, ArH
and CH@CH), 7.82–8.10 (m, 10H, ArH and CH@CH), 8.23 (d, 1H,
J = 8.0 Hz, ArH), 8.38 (s, 1H, ArH), 8.74 (s, 1H, ArH), 10.45 (s, 1H,
NH); m/z = 457.30 (m+1).
4.3.17. Cyclopropanecarboxylic acid {3-[3-(9-methyl-9H-
carbazol-3-yl)-acryloyl]-phenyl}-amide (7q)
4.3.11. 4-Methyl-N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-
phenyl}-benzamide (7k)
Yield 83%; Mp: 185–189 °C; IR (KBr, cmÀ1): 3300, 2930, 1656,
1559, 1434, 1204, 1104, 1016, 955, 778, 688; 1H NMR (400 MHz,
DMSO-d6, d in ppm): 0.83 (m, 4H, cyclopropyl (CH2)2), 1.81 (m,
1H, cyclopropyl CH), 3.94 (s, 3H, NCH3), 7.28 (t, 1H, J = 8.0 Hz,
ArH), 7.58 (t, 2H, J = 8.0 Hz, ArH), 7.65 (d, 1H, J = 15.2 Hz, CH@CH),
7.70 (d, 1H, J = 15.2 Hz, CH@CH), 7.85–8.05 (m, 5H, ArH), 8.20–8.26
(m, 2H, ArH), 8.74 (s, 1H, ArH), 10.45 (s, 1H, NH); m/z = 395.25
(m+1).
Yield 80%; Mp: 190–192 °C; IR (KBr, cmÀ1): 3310, 3130, 2972,
1673, 1618, 1586, 1530, 1420, 1012, 925, 860; 1H NMR
(400 MHz, DMSO-d6, d in ppm): 2.40 (s, 3H, CH3), 3.90 (s, 3H,
NCH3), 7.29 (t, 1H, J = 8.0 Hz, ArH), 7.52 (t, 1H, J = 8.0 Hz, ArH),
7.59 (t, 1H, J = 8.4 Hz, ArH), 7.63–7.68 (m, 3H, ArH and CH@CH),
7.69 (d, 1H, J = 8.4 Hz, ArH), 7.90 (d, 1H, J = 15.2 Hz, CH@CH),
7.98–8.05 (m, 5H, ArH), 8.13 (d, 1H, J = 8.0 Hz, ArH), 8.23 (d, 1H,
J = 8.0 Hz, ArH), 8.44 (s, 1H, ArH), 8.74 (s, 1H, ArH), 10.50 (s, 1H,
NH); m/z = 445.30 (m+1).
4.3.18. N-{3-[3-(9-Methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-
acetamide (7r)
4.3.12. 4-tert-Butyl-N-{3-[3-(9-methyl-9H-carbazol-3-yl)-
acryloyl]-phenyl}-benzamide (7l)
Yield 88%; Mp: 160–164 °C; IR (KBr, cmÀ1): 3300, 2930, 1656,
1559, 1434, 1204, 1104, 1016, 955, 778, 688; 1H NMR (400 MHz,
DMSO-d6, d in ppm): 2.09 (s, 3H, CH3), 3.94 (s, 3H, NCH3), 7.28 (t,
1H, J = 8.0 Hz, ArH), 7.58 (t, 2H, J = 8.0 Hz, ArH), 7.65 (d, 1H,
J = 15.2 Hz, CH@CH), 7.70 (d, 1H, J = 15.2 Hz, CH@CH), 7.85–8.05
(m, 5H, ArH), 8.20–8.26 (m, 2H, ArH), 8.73 (s, 1H, ArH), 10.17 (s,
1H, NH); m/z = 369.20 (m+1).
Yield 65%; Mp: 144–146 °C; IR (KBr, cmÀ1): 3353, 3061, 2958,
1649, 1618, 1585, 1543, 1458, 1410, 1016, 918, 850, 761; 1H
NMR (400 MHz, DMSO-d6, d in ppm): 1.35 (s, 9H, C(CH3)3), 3.94
(s, 3H, NCH3), 7.28 (t, 1H, J = 8.0 Hz, ArH), 7.50 (t, 1H, J = 8.0 Hz,
ArH), 7.56–7.61 (m, 3H, ArH), 7.64 (d, 1H, J = 8.0 Hz, ArH), 7.69
(d, 1H, J = 8.4 Hz, ArH), 7.88–8.04 (m, 6H, ArH and CH@CH), 8.14
(d, 1H, J = 8.0 Hz, ArH), 8.23 (d, 1H, J = 8.0 Hz, ArH), 8.45 (s, 1H,
ArH), 8.75 (s, 1H, ArH), 10.41 (s, 1H, NH); m/z = 487.40 (m+1).
4.4. Synthesis of (E)-1-(3-aminophenyl)-3-(9-methyl-9H-
carbazol-3-yl)-prop-2-en-1-one (8)
4.3.13. N-{3-[3-(9-Methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-
3-trifluoromethyl-benzamide (7m)
3-Aminoacetophenone 4 (1 mmol) was dissolved in ethanol
(15 ml), 1 ml 20% NaOH solution was added to it and stirred for
10 min at room temperature. Then, 3-formyl-9-methylcarbazole
3 (1 mmol) was added and stirring continued for 24 h at room
Yield 88%; Mp: 119–122 °C; IR (KBr, cmÀ1): 3325, 3048, 2946,
2743, 1673, 1636, 1545, 1453, 1392, 1231, 1138, 1040, 894, 776;