Bangladesh J Pharmacol 2015; 10: 230-240
233
-1 1
-1 1
1
d
483, 1430 (aromatics) cm ; H NMR (300 MHz, acetone-
): δ 7.16 (2H, d, J=7.8 Hz, H-4’’, H-12’’), 7.23 (2H, m, H
1523, 1458, 1420 (aromatics) cm ; H NMR (300 MHz,
DMSO-d ): δ 4.64 (2H, d, J=5.1 Hz, H -7’’), 5.26 (1H, dd,
6
6
2
-
(
5’, H-6’), 7.26 (4H, m, H-5’’, H-6’’, H-10’’, H-11’’), 7.44
1H, d, J=2.1 Hz, H-8’’), 7.51 (1H, dd, J=8.1, 2.1 Hz, H-
J=10.5, 0.9 Hz, Ha-9’’), 5.40 (1H, dd, J=17.4, 1.5 Hz, Hb-
9’’), 6.05 (1H, m, H-8’’), 7.24 (3H, m, H-5’, H-6’, H-4’’),
7.49 (2H, d, J=8.1 Hz, H-4’, H-5’’), 7.54 (1H, s, H-2’’),
7.60 (1H, d, J=15.6 Hz, H-2), 8.03 (1H, d, J=6.6 Hz, H-7’),
4
’), 7.59 (2H, d, J=7.8 Hz, H-3’’, H-13’’), 7.87 (1H, d,
J=15.6 Hz, H-2), 7.89 (1H, brs, H-2’), 8.21 (1H, dd, J=8.1,
.1 Hz, H-7’), 8.55 (1H, d, J=15.6 Hz, H-3), 13.05 (1H,
2
8.06 (1H, d, J=15.6 Hz, H-3), 8.09 (1H, d, J=2.1 Hz, H-2’),
13
13
brs, NH); C NMR (75 MHz, acetone-d
6
): δ 111.65 (C-
7.70 (1H, d, J=8.1 Hz, H-6’’), 9.90 (1H, brs, NH);
NMR (75 MHz, DMSO-d
C
5
1
6
1
1
1
’’, C-11’’), 112.53 (C-4’’, C-12’’), 113.06 (C-4’), 114.23 (C-
6
): δ 69.20 (C-7’’), 113.42 (C-4’),
a
a
’), 116.45 (C-3’’, C-13’’), 121.11 (C-7’), 121.89 (C-2, C-
113.60 (C-1’), 114.44 (C-2’’), 116.31 (C-2), 118.42 (C-9’’),
119.82 (C-4’’), 121.09 (C-7’), 121.59 (C-6’’), 122.07 (C-6’),
123.59 (C-5’), 126.05 (C-3’), 130.72 (C-5’’), 134.10 (C-2’),
134.39 (C-8’’), 138.44 (C-8’), 140.08 (C-3), 140.90 (C-1’’),
159.25 (C-3’’), 189.60 (C-1); ESI-MS, MeOH (Positive):
b
b
’), 123.15 (C-6’’, C-10’’), 123.48 (C-5’), 124.15 (C-8’’),
26.40 (C-3’), 128.15 (C-1’’), 133.50 (C-2’), 138.88 (C-8’),
39.30 (C-3), 155.35 (C-7’’, C-9’’), 155.91 (C-2’’, C-14’’),
c
c
79.72 (C-1) (a,b,c=interchangable); ESI-MS, MeOH
+
-
+
-
(
Positive): m/z 348 [M+H] , 346[M-H] , C25
H17NO.
2
m/z 304[M+H] , Negative: 302[M-H] , C20H17NO .
Trans-3-(1H-indol-3-yl)-1-(benzofuran)-2-propen-1-one
Trans-3-(1H-indol-3-yl)-1-(4’-allyloxyphenyl)-2-
propen-1-one (1i)
(
1d)
Dark brown solid; 40%, yield; mp 59-60°C; IR νmax
Light brown powder; 30%; mp 110-111°C; IR νmax (KBr):
(
KBr): 3395, 1151, 1156, 736 (NH), 1654 (chalcone C=O),
3372 1561, 1205, 736 (NH), 1651 (chalcone C=O), 1511,
-1 1
1470, 1406 (aromatics) cm-1
;
1
H NMR (300 MHz, DMSO-
1
509, 1483, 1427 (aromatics) cm ; H NMR (300 MHz,
): δ 7.11 (2H, m, H-5’, H-6’), 7.35 (1H, d,
J=15.6 Hz, H-2), 7.49 (3H, m, H-4’, H-5’’, H-6’’), 7.53
acetone-d
6
d
6
): δ 4.65 (2H, d, J=5.04 Hz, H -7’’), 5.28 (1H, d, J=10.52
2
Hz, Hb-9’’), 5.42 (1H, d, J=17.21 Hz, Ha-9’’), 6.05 (1H, m,
H-8’’), 7.08 (2H, d, J=8.64 Hz, H-3’’, H-5’’), 7.24 (1H, m,
H-5’, H-6’), 7.53 (1H, m, H-4’), 7.67 (1H, d, J=15.40 Hz,
H-2), 8.06 (1H d, J=15.56 Hz, H-3), 8.09 (2H, m, H-2’, H-
7’), 8.13 (1H, d, J=8.72 Hz, H-2’’), 8.13 (1H, d, J=8.72 Hz,
H-6’’), 9.91 (1H, brs, NH); 13C NMR (75 MHz, DMSO-
(
(
1H, d, J=15.6 Hz, H-3), 7.61 (1H, d, J=2.7 Hz, H-2’), 7.92
1H, dd, J=8.4, 2.1 Hz, H-7’), 8.01 (1H, dd, J=6.9, 2.7 Hz,
H-4’’), 8.12 (1H, dd, J=7.2, 2.4 Hz, H-8’’), 8.62 (1H, s, H-
2
δ 112.92 (C-4’), 113.31 (C-1’), 120.69 (C-2), 121.86 (C-
7
1
3
8
(
2
1
3
’’), 13.05 (1H, brs, NH); C NMR (75 MHz, acetone-d
6
):
a
a
b
d6): δ 68.86 (C-7’’), 113.00 (C-4’), 113.19 (C-1’), 115.02 (C-
3’’, C-5’’), 115.66 (C-2), 118.36 (C-9’’), 120.74 (C-7’),
121.53 (C-6’), 123.07 (C-5’), 125.66 (C-3’), 130.85 (C-6’’),
131.80 (C-1’’), 130.85 (C-2’’), 133.37 (C-2’), 133.65 (C-8’’),
138.06 (C-8’), 138.74 (C-3), 162.05 (C-4’’), 187.76 (C-1);
’), 123.42 (C-6’), 124.71 (C-5’), 125.71 (C-3’, C-2’’),
b
25.91 (C-7’’), 126.66 (C-4’’), 127.96 (C-5’’), 128.72 (C-
c
’’), 129.05 (C-6’’), 131.76 (C-8’’) 133.17 (C-2’), 136.65 (C-
’), 138.47c (C-1’’), 142.74 (C-3), 198.91 (C-1),
a,b,c=interchangable); ESI-MS, MeOH (Positive): m/z
+
-
ESI-MS, MeOH (Positive): m/z 304[M+H]
+
, Negative:
2
88[M+H] , Negative: 286[M-H] , C19H13NO .
-
3
02[M-H] , C20
H17NO
2
.
Trans-3-(1H-indol-3-yl)-1-(4’-chlorophenyl)-2-propen-
-one (1e)
1
Trans-3 -(1 H -indo l -3 -yl )-1 - (4 ’ -ally lox y - 2 ’-
hydroxyphenyl)-2-propen-1-one (1j)
Yellow fluffy crystals, 60% yield, obtained and analysed
by spectroscopic data as described by an earlier method
(
Yellow powder; 30% yield; mp 110-111°C; IR νmax (KBr):
3
569 1559, 1229, 735 (NH), 3380 (OH), 1621 (chalcone
Black., et al 1992).
-1 1
C=O), 1497, 1439, 1369 (aromatics) cm ; H NMR (300
MHz, DMSO-d ): δ 4.65 (2H, d, J=4.92 Hz, H -7’’), 5.29
1H, d, J=10.68 Hz, Hb-9’’), 5.42 (1H, d, J=17.32 Hz, Ha-
Trans-3-(1H-indol-3-yl)-1-(2’-chlorophenyl)-2-propen-
1
6
2
-one (1f)
(
9
’’), 6.04 (1H, m, H-8’’), ), 6.50 (1H, s, H-3’’), 6.58 (1H,
Yellow shiny crystals, 85% yield, obtained and analysed
by spectroscopic data as described by an earlier method
dd, J=8.92, 2.08 Hz, H-5’’), 7.25 (2H, m, H-5’, H-6’), 7.52
dd, J=7.92, 2.52 Hz, H-4’), 7.54 (1H, dd, J=7.92, 2.52 Hz,
H-4’), 7.68 (1H, d, J=15.3 Hz, H-2), 8.11 (1H, dd, J=7.92,
.52 Hz, H-7’), 8.14 (1H, s, H-2’), 8.17 (1H, d, J=15.3 Hz,
(
(Black., et al 1992).
Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen
2
-1-one (1g)
13
H-3), 8.19 (1H, m, H-6’’), 9.45 (1H, brs, NH); C NMR
(
(
(
(
(
(
[
6
75 MHz,DMSO-d ): δ 69.00 (C-7’’), 113.10 (C-4’), 113.36
Light brown crystals, 55% yield, obtained and analysed
by spectroscopic data as described by an earlier method
C-1’), 102.20 (C-3’’), 107.93 (C-5’’), 114.11 (C-2), 114.51
C-1’’), 118.46 (C-9’’), 120.85 (C-7’), 121.81 (C-6’), 123.30
C-5’), 125.63 (C-3’), 132.46 (C-6’’), 165.89 (C-2’’), 134.43
C-2’), 133.47 (C-8’’), 138.14 (C-8’), 139.90 (C-3), 164.43
C-4’’), 192.08 (C-1); ESI-MS, MeOH (Positive): m/z 320
(Black., et al 1992).
Trans-3-(1H-indol-3-yl)-1-(3’-allyloxyphenyl)-2-
propen-1-one (1h)
+
-
3
M+H] , Negative: 318[M-H] , C20H17NO .
Light brown powder; 65% yield; mp 90-92°C;IR νmax
(KBr): 3389 1564, 1211, 739 (NH), 1653 (chalcone C=O),
Synthesis of indolyl chalcones 2(a–k)