136
N. Shankaraiah et al. / Bioorganic Chemistry 59 (2015) 130–139
DMSO-d6): d 3.95 (s, 6H), 3.96 (s, 6H), 3.97 (s, 3H), 3.98 (s, 3H), 7.23
(s, 2H), 7.36 (t, 1H, J = 7.5 Hz), 7.38 (s, 1H), 7.59 (t, 1H, J = 7.5 Hz),
7.62 (d, 1H, J = 8.3 Hz), 8.06 (d, 1H, J = 15.1 Hz), 8.12 (d, 1H,
J = 8.3 Hz), 8.15 (d, 1H, J = 15.1 Hz), 8.18 (s, 1H), 8.20 (d, 1H,
J = 7.5 Hz), 11.20 (brs, 1H); 13C NMR (75 MHz, DMSO-d6): d 188.3,
153.1, 152.7, 144.5, 142.5, 142.7, 142.1, 141.3, 138.3, 133.7, 133.6,
133.5, 129.6, 127.8, 121.3, 121.5, 120.9, 119.7, 112.4, 106.0, 105.8,
95.7, 60.1, 60.1, 55.8, 55.6; HRMS (ESI): m/z calcd. for C32H31N2O7
555.2131 found 555.2155 [M + H]+.
141.5, 140.9, 140.5, 132.7, 130.0, 129.7, 129.6, 128.9, 127.2,
120.3, 119.0, 115.3, 114.6, 114.4, 112.7, 111.6, 54.3; HRMS (ESI):
m/z calcd. for C27H20N2O2F 423.1508, found 423.1551 [M + H]+.
4.2.1.8.
(E)-3-(1-(4-Fluorophenyl)-9H-pyrido[3,4-b]indol-3-yl)-1-
(3,4,5-trimethoxy phenyl)prop-2-en-1-one (7h). Mp: 164–165 °C;
FT-IR (cmÀ1) 3495, 2934, 1648, 1567, 1502, 1455, 1415, 1332,
1226, 1158, 1124, 986, 839, 751; 1H NMR (300 MHz, DMSO-d6): d
3.87 (s, 3H), 3.96 (s, 6H), 7.29 (d, 2H, J = 8.3 Hz), 7.30 (t, 1H,
J = 7.5 Hz), 7.34 (s, 2H), 7.50 (t, 1H, J = 7.5 Hz), 7.64 (d, 1H,
J = 8.3 Hz), 7.96 (d, 1H, J = 15.1 Hz), 8.07 (d, 1H, J = 15.1 Hz), 8.14
(d, 2H, J = 8.3 Hz), 8.17 (d, 1H, J = 7.5 Hz), 8.25 (s, 1H), 11.43 (brs,
1H); 13C NMR (75 MHz, DMSO-d6): d 187.3, 151.8, 143.6, 141.0,
140.6, 140.5, 132.6, 132.5, 129.6, 129.5, 128.9, 126.9, 120.7,
120.2, 120.1, 118.8, 115.1, 114.1, 111.5, 105.0, 94.8, 59.2, 54.9;
4.2.1.3. (E)-1-(4-Fluorophenyl)-3-(1-(3,4,5-Trimethoxyphenyl)-9H-
pyrido[3,4-b]indol-3-yl)prop-2-en-1-one (7c). Mp: 139–140 °C; FT-
IR (cmÀ1) 3314, 2934, 1677, 1593, 1501, 1453, 1386, 1324, 1153,
1125, 1003, 838, 747; 1H NMR (300 MHz, DMSO-d6): d 3.89 (s,
3H), 4.02 (s, 6H), 7.28 (s, 2H), 7.28 (t, 1H, J = 7.5 Hz), 7.52 (t, 1H,
J = 7.5 Hz), 7.65 (d, 1H, J = 7.5 Hz), 7.82 (s, 1H), 8.02 (d, 1H,
J = 15.1 Hz), 8.10 (d, 1H, J = 15.1 Hz), 8.17 (d, 1H, J = 7.5 Hz), 8.29
(d, 2H, J = 8.3 Hz), 8.39 (d, 2H, J = 8.3 Hz), 11.20 (brs, 1H); HRMS
(ESI): m/z calcd. for C29H24N2O4F 483.1720 found 483.1723 [M + H]+.
HRMS (ESI): m/z calcd. for
C29H24N2O4F 483.1720, found
483.1703 [M + H]+.
4.2.1.9. (E)-1-(4-Fluorophenyl)-3-(1-(4-fluorophenyl)-9H-pyrido[3,4-
b]indol-3-yl) prop-2-en-1-one (7i). Mp: 220–221 °C; FT-IR (cmÀ1
)
4.2.1.4. (E)-3-(1-(3,4,5-Trimethoxyphenyl)-9H-pyrido[3,4-b]indol-3-
yl)-1-(4-nitrophenyl)prop-2-en-1-one (7d). Mp: 285–286 °C; FT-IR
(cmÀ1) 3294, 2935, 1658, 1588, 1513, 1459, 1382, 1314, 1237,
1129, 1026, 847, 746; 1H NMR (300 MHz, DMSO-d6): d 3.90 (s,
3H), 4.03 (s, 6H), 7.32 (s, 2H), 7.31 (t, 1H, J = 7.5 Hz), 7.55 (t, 1H,
J = 7.5 Hz), 7.68 (d, 1H, J = 8.1 Hz), 8.07 (d, 1H, J = 15.1 Hz), 8.20
(d, 1H, J = 7.9 Hz), 8.14 (d, 1H, J = 15.1 Hz), 8.27 (d, 2H, J = 8.6 Hz),
8.34 (d, 2H, J = 8.6 Hz), 8.36 (s, 1H), 11.20 (brs, 1H); HRMS (ESI):
m/z calcd. for C29H24N3O6 510.1665 found 510.1680 [M + H]+.
3294, 2925, 1654, 1601, 1566, 1503, 1455, 1378, 1320, 1235,
1153, 1030, 836, 746; 1H NMR (300 MHz, DMSO-d6): d 7.19 (d,
2H, J = 8.4 Hz), 7.29 (t, 1H, J = 7.4 Hz), 7.33 (d, 2H, J = 8.6 Hz), 7.51
(t, 1H, J = 7.4 Hz), 7.63 (d, 1H, J = 7.9 Hz), 7.98 (d, 1H, J = 15.1 Hz),
8.16 (d, 1H, J = 7.9 Hz), 8.15 (d, 2H, J = 8.3 Hz), 7.09 (d, 1H,
J = 15.1 Hz), 8.17 (d, 2H, J = 8.4 Hz), 8.22 (s, 1H), 11.43 (brs, 1H);
13C NMR (75 MHz, DMSO-d6): d 186.7, 165.5, 163.2, 162.2, 159.9,
143.7, 140.6, 140.3, 133.5, 132.5, 129.7, 129.6, 129.5, 129.4,
128.6, 126.8, 120.2, 119.9, 120.1, 118.7, 115.3, 114.2, 113.9,
111.4, 94.7; HRMS (ESI): m/z calcd. for C26H17N2OF2 411.1308,
found 411.1313 [M + H]+.
4.2.1.5.
(E)-1-(4-Aminophenyl)-3-(1-(3,4,5-trimethoxyphenyl)-9H-
pyrido[3,4-b]indol-3-yl)prop-2-en-1-one (7e). Mp: 231–232 °C; FT-
IR (cmÀ1) 3401, 3258, 3001, 2927, 1647, 1614, 1582, 1509, 1459,
1427, 1312, 1279, 1231, 1127, 1037, 997, 820, 753; 1H NMR
(300 MHz, DMSO-d6): d 3.95 (s, 3H), 3.96 (s, 6H), 4.14 (brs, 2H),
6.68 (d, 2H, J = 8.4 Hz), 7.18 (s, 2H), 7.35 (t, 1H, J = 7.5 Hz), 7.55
(t, 1H, J = 7.5 Hz), 7.57 (d, 1H, J = 8.1 Hz), 7.96 (d, 1H, J = 15.1 Hz),
8.01 (d, 2H, J = 8.4 Hz), 8.10 (d, 1H, J = 15.1 Hz), 8.14 (d, 1H,
J = 7.9 Hz), 8.20 (s, 1H), 11.10 (brs, 1H); 13C NMR (75 MHz,
DMSO-d6): d 186.0, 153.7, 153.0, 142.7, 142.4, 142.5, 141.3,
138.0, 133.2, 133.4, 130.8, 129.5, 128.2, 125.5, 122.1, 121.1.5,
121.0, 119.9, 115.2, 112.6, 112.8, 59.9, 55.8 HRMS (ESI): m/z calcd.
for C29H26N3O4 480.1923 found 480.1925 [M + H]+.
4.2.1.10. (E)-3-(1-(4-Fluorophenyl)-9H-pyrido[3,4-b]indol-3-yl)-1-(4-
nitrophenyl) prop-2-en-1-one (7j). Mp: 244–245 °C; FT-IR (cmÀ1
)
3355, 2927, 1651, 1605, 1502, 1449, 1312, 1235, 1167, 1024, 834,
730; 1H NMR (300 MHz, DMSO-d6): d 7.32 (d, 2H, J = 8.4 Hz), 7.40
(t, 1H, J = 7.5 Hz), 7.56 (t, 1H, J = 7.5 Hz), 7.62 (d, 1H, J = 7.9 Hz),
7.98 (d, 1H, J = 15.1 Hz), 8.04 (d, 2H, J = 8.4 Hz), 8.14 (d, 1H,
J = 8.3 Hz), 8.09 (d, 1H, J = 15.1 Hz), 8.25 (d, 2H, J = 8.8 Hz), 8.37 (d,
2H, J = 8.8 Hz) 8.42 (s, 1H), 11.64 (brs, 1H); 13C NMR (75 MHz,
DMSO-d6): d 187.0, 148.0, 145.0, 141.5, 140.4, 140.1, 139.9, 133.2,
132.8, 132.8, 129.2, 129.1, 128.2, 127.9, 126.8, 122.1, 119.8, 119.6,
118.6, 115.7, 114.2, 113.8, 111.2; HRMS (ESI): m/z calcd. for
C
26H17N3O3F 438.1253, found 438.1267 [M + H]+.
4.2.1.6. (E)-1-(4-Hydroxyphenyl)-3-(1-(3,4,5-trimethoxyphenyl)-9H-
pyrido[3,4-b]indol-3-yl)prop-2-en-1-one (7f). Mp: 304–305 °C; FT-
IR (cmÀ1) 3422, 3214, 2933, 1726, 1592, 1502, 1458, 1385, 1330,
1234, 1165, 1120, 1034, 984, 839, 749; 1H NMR (300 MHz,
DMSO-d6): d 3.80 (s, 3H), 3.95 (s, 6H), 6.95 (d, 2H, J = 8.4 Hz), 7.30
(s, 2H), 7.34 (t, 1H, J = 7.5 Hz), 7.60 (t, 1H, J = 7.5 Hz), 7.67 (d, 1H,
J = 8.1 Hz), 7.94 (d, 1H, J = 15.1 Hz), 8.07 (d, 3H, J = 8.4 Hz), 8.20 (d,
1H, J = 15.1 Hz), 8.31 (d, 1H, J = 8.1 Hz), 8.72 (s, 1H), 10.44 (brs,
1H); 13C NMR (75 MHz, DMSO-d6): 187.0, 161.8, 153.8, 143.5,
142.4, 142.1, 141.0, 137.7, 133.1, 130.7, 129.2, 129.0, 128.1, 121.3,
120.8, 119.8, 115.1, 112.5, 105.5, 59.7, 55.5; HRMS (ESI): m/z calcd.
for C29H25N2O5 481.1763 found 481.1763 [M + H]+.
4.2.1.11. (E)-1-(4-Aminophenyl)-3-(1-(4-fluorophenyl)-9H-pyri-
do[3,4-b]indol-3-yl) prop-2-en-1-one (7k). Mp: 152–153 °C; FT-IR
(cmÀ1) 3335, 3220, 2924, 1660, 1593, 1501, 1445, 1279, 1233,
1169, 1016, 834, 746; 1H NMR (300 MHz, DMSO-d6): d 6.56 (d,
2H, J = 8.4 Hz), 6.67 (d, 2H, J = 8.4 Hz), 7.25 (t, 2H, J = 7.5 Hz), 7.35
(d, 2H, J = 8.6 Hz), 7.52 (t, 2H, J = 7.5 Hz), 7.86 (d, 1H, J = 15.1 Hz),
7.87 (d, 1H, J = 8.3 Hz), 8.10 (d, 1H, J = 15.1 Hz), 8.14 (d, 2H,
J = 8.3 Hz), 8.17 (d, 1H, J = 8.4 Hz), 8.30 (s, 1H), 11.62 (brs, 1H);
13C NMR (75 MHz, DMSO-d6): d 186.2, 152.9, 152.8, 142.5, 142.1,
130.4, 130.4, 130.3, 130.0, 129.60, 127.6, 125.9, 121.9, 120.9,
119.5, 115.4, 115.2, 114.9, 112.6, 112.4, 112.2, 95.5; HRMS (ESI):
m/z calcd. for C26H19N3OF 408.1512, found 408.1507 [M + H]+.
4.2.1.7. (E)-3-(1-(4-Fluorophenyl)-9H-pyrido[3,4-b]indol-3-yl)-1-(4-
methoxyphenyl) prop-2-en-1-one (7g). Mp: 190–191 °C; FT-IR
(cmÀ1) 3355, 2926, 1651, 1605, 1503, 1448, 1309, 1235, 1168,
1024, 835, 732; 1H NMR (300 MHz, DMSO-d6): d 3.90 (s, 3H),
7.00 (d, 2H, J = 8.8 Hz) 7.31 (d, 2H, J = 8.4 Hz), 7.36–7.40 (t, 1H,
J = 7.5 Hz), 7.56 (t, 1H, J = 7.5 Hz), 8.02 (d, 1H, J = 15.1 Hz), 8.05
(d, 1H, J = 7.9 Hz), 8.10 (d, 2H, J = 8.3 Hz), 8.14 (d, 1H, J = 15.1 Hz),
8.17 (d, 2H, J = 8.4 Hz), 8.22 (d, 1H, J = 8.4 Hz), 8.34 (s, 1H), 10.62
(brs, 1H); 13C NMR (75 MHz, DMSO-d6): d 187.4, 162.1, 143.0,
4.2.1.12.
(E)-1-(3,4,5-Trimethoxyphenyl)-3-(1-(3,4-dimethoxyphe-
nyl)-9H-pyrido[3,4-b]indol-3-yl)prop-2-en-1-one (7m). Mp: 157–
159 °C; FT-IR: (cmÀ1) 3273, 2923, 2845, 1650.61, 1572.30, 1508,
1448, 1334, 1241, 1130, 1024, 837, 744; 1H NMR (300 MHz,
DMSO-d6): d 3.83 (s, 3H), 3.94 (s, 9H), 3.99 (s, 3H), 7.16 (d, 1H,
J = 7.3 Hz), 7.30 (t, 1H, J = 7.5 Hz), 7.40 (s, 2H), 7.54 (t, 1H,
J = 7.5 Hz), 7.68 (d, 2H, J = 7.3 Hz), 7.70 (s, 1H), 7.99 (d, 1H,
J = 15.1 Hz), 8.09 (d, 1H, J = 7.3 Hz), 8.16 (d, 1H, J = 15.1 Hz), 8.24