Med Chem Res
1
6.58 (s, 1H, H-furan), 6.33 (d, J = 10.0 Hz, 1H, H-pyrano),
4.65 (t, J = 5.6 Hz, 2H, –OCH2CH2), 3.70 (t, J = 4.6 Hz,
4H, –N(CH2CH2)2O) 2.94 (t, J = 5.6 Hz, 2H, –OCH2CH2),
2.63 (s, 4H, –N(CH2CH2)2O); 13C-NMR (101 MHz, CDCl3):
d 159.27, 158.88 (JC–F = 249.47 Hz), 146.65, 145.82,
143.23, 141.47, 131.54 (JC–F = 2.02 Hz), 130.91, 129.84
(JC–F = 8.08 Hz), 125.36, 123.67 (JC–F = 4.04 Hz), 121.98
(JC–F = 16.16 Hz), 119.36, 115.46 (JC–F = 22.22 Hz),
113.98, 113.82, 105.71, 70.23, 66.09, 57.59, 53.05; EI–MS
(m/z): 409.1 [M]?.
1001, 829, 754, 702 cm-1; H-NMR (400 MHz, CDCl3): d
7.63 (d, J = 2.0 Hz, 1H, H-furan), 7.60 (d, J = 10.0 Hz, 1H,
H-pyrano), 7.53–7.46 (m, 2H, ArH), 7.41 (d, J = 7.2 Hz, 4H,
ArH), 7.35–7.31 (m, 2H, ArH), 7.31–7.27 (m, 2H, ArH), 7.24
(s, 2H, ArH), 7.16 (t, J = 7.2 Hz, 2H, ArH), 6.56 (s, 1H,
H-furan), 6.31 (d, J = 10.0 Hz, 1H, H-pyrano), 4.64 (t,
J = 5.6 Hz, 2H, –OCH2CH2), 4.17 (s, 1H, NCH(Ph)2), 2.94
(t, J = 5.8 Hz, 2H, –OCH2CH2), 2.64 (s, 4H, –CH2N(CH2
CH2)2NCH–), 2.40 (s, 4H, –CH2N(CH2CH2)2NCH–); 13C-
NMR (101 MHz, CDCl3): d 160.32, 159.88 (JC–F
=
249.47 Hz), 147.55, 146.79, 144.14, 142.92, 142.44, 132.58
(JC–F = 249.47 Hz), 131.98, 130.79 (JC–F = 8.08 Hz),
128.56, 128.04, 126.97, 126.35, 124.64 (JC–F = 4.04 Hz),
4-(2-chlorophenyl)-9-(2-morpholinoethoxy)-7H-
furo[3,2-g]chromen-7-one (13d)
123.04 (JC–F = 16.16 Hz), 120.13, 116.44 (JC–F
=
Yield 60 %; White solid; m.p. 117–118 °C; Rf = 0.40
(petroleum ether:ethyl acetate = 2:1); IR (KBr): mmax
3117, 3062, 2957, 2854, 1734, 1589, 1458, 1375, 1311,
22.22 Hz),114.94,114.78, 106.62, 76.33,71.34,58.11,53.86,
51.94; EI–MS (m/z): 574.2 [M]?.
1
1150, 1109, 1030, 831, 758 cm-1; H-NMR (400 MHz,
4-(2-chlorophenyl)-9-(2-(4-benzhydrylpiperazin-1-
CDCl3): d 7.66 (d, J = 2.0 Hz, 1H, H-furan), 7.59 (d,
J = 7.6 Hz, 1H, H-pyrano), 7.53–7.37 (m, 3H, ArH), 7.32
(d, J = 7.2 Hz, 1H, ArH), 6.48 (d, J = 2.0 Hz, 1H,
H-furan), 6.31 (d, J = 9.8 Hz, 1H, H-pyrano), 4.67 (t,
J = 5.6 Hz, 2H, –OCH2CH2), 3.70 (t, J = 4.4 Hz, 4H,
–N(CH2CH2)2O), 2.94 (t, J = 5.6 Hz, 2H, –OCH2CH2),
2.63 (s, 4H, –N(CH2CH2)2O); 13C-NMR (101 MHz,
CDCl3): d 160.33, 147.54, 146.77, 143.99, 142.42, 134.27,
132.39, 131.83, 130.24, 127.31, 127.17, 126.09, 123.84,
114.89, 114.79, 106.70, 106.63, 71.20, 67.10, 58.62, 54.06;
EI–MS (m/z): 425.0 [M]?.
yl)ethoxy)-7H-furo[3,2-g]chromen-7-one (13f)
Yield 63 %; Yellow solid; m.p. 87–88 °C; Rf = 0.24
(petroleum ether:ethyl acetate = 2:1); IR (KBr): mmax 3150,
3070, 2955, 2810, 1736, 1589, 1456, 1375, 1311, 1150, 1099,
1
1003, 833, 754, 704 cm-1; H-NMR (400 MHz, CDCl3): d
7.62 (d, J = 2.0 Hz, 1H, H-furan), 7.59 (d, J = 7.8 Hz, 1H,
H-pyrano), 7.50–7.45 (m, 2H, ArH),7.41 (d, J = 7.2 Hz, 4H,
ArH), 7.36–7.30 (m, 2H, ArH), 7.28 (s, 2H, ArH),7.24 (s, 2H,
ArH), 7.16(t, J = 7.2 Hz, 2H, ArH), 6.45(d, J = 2.0 Hz, 1H,
H-furan), 6.28 (d, J = 10.0 Hz, 1H, H-pyrano), 4.65 (t,
J = 5.6 Hz, 2H, –OCH2CH2), 4.19 (s, 1H, NCH(Ph)2), 2.95
(t, J = 5.8 Hz, 2H, –OCH2CH2), 2.64 (s, 4H, –CH2N(CH2
CH2)2NCH–), 2.40 (s, 4H, –CH2N(CH2CH2)2NCH–); 13C-
NMR (101 MHz, CDCl3): d 160.36, 147.47, 146.74, 146.65,
143.93, 142.94, 142.38, 134.35, 132.42, 131.93, 130.24,
130.19, 128.57, 128.05, 127.13, 126.98, 126.08, 123.62,
114.87, 114.77, 106.55, 76.36, 71.35, 58.17, 53.89, 51.96; EI–
MS (m/z): 590.3 [M]?.
4-(2-bromophenyl)-9-(2-morpholinoethoxy)-7H-furo[3,2-
g]chromen-7-one (14d)
Yield 58 %; Light brown solid; m.p. 121–122 °C; Rf = 0.23
(dichloromethane:ethyl acetate = 2:1); IR (KBr): mmax 3151,
3060, 2957, 2810, 1732, 1589, 1429, 1375, 1312, 1269, 1150,
1109, 1030, 833, 756 cm-1; 1H-NMR (400 MHz, CDCl3): d
7.77 (d, J = 8.0 Hz, 1H, H-pyrano), 7.66 (d, J = 2.4 Hz, 1H,
H-furan), 7.49–7.35 (m, 3H, ArH), 7.31 (d, J = 7.6 Hz, 1H,
ArH), 6.48(d, J = 2.0 Hz, 1H, H-furan), 6.33(d, J = 9.6 Hz,
1H, H-pyrano), 4.66(t, J = 5.4 Hz, 2H, –OCH2CH2), 3.70(d,
J = 4.4 Hz, 4H, –N(CH2CH2)2O), 2.93 (t, J = 5.6 Hz, 2H,
–OCH2CH2), 2.64 (s, 4H, –N(CH2CH2)2O); 13C-NMR
(101 MHz,CDCl3):d160.34, 147.50, 146.74, 143.92, 142.40,
133.39, 132.29, 132.27, 132.17, 130.37, 128.69, 128.56,
127.74, 125.95, 124.47, 114.78, 106.61, 71.22, 67.11, 58.63,
54.07; EI–MS (m/z): 469.0 [M]?.
4-(2-bromophenyl)-9-(2-(4-benzhydrylpiperazin-1-
yl)ethoxy)-7H-furo[3,2-g]chromen-7-one (14f)
Yield 60 %; White solid; m.p. 65–66 °C; Rf = 0.24
(petroleum ether:ethyl acetate = 2:1); IR (KBr): mmax
3150, 3080, 2953, 2808, 1734, 1587, 1429, 1310, 1150,
;
1093, 1027, 831, 752, 700 cm-1 1H-NMR (400 MHz,
CDCl3): d 7.77 (d, J = 7.6 Hz, 1H, H-pyrano), 7.62 (d,
J = 2.4 Hz, 1H, H-furan), 7.49–7.34 (m, 8H, ArH), 7.32-
7.27 (m, 2H, ArH), 7.24 (s, 2H, ArH), 7.16 (t, J = 7.2 Hz,
2H, ArH), 6.43 (d, J = 2.0 Hz, 1H, H-furan), 6.28 (d,
J = 9.6 Hz, 1H, H-pyrano), 4.67 (t, J = 5.6 Hz, 2H,
–OCH2CH2), 4.20 (s, 1H, NCH(Ph)2), 2.97 (t, J = 5.0 Hz,
2H, –OCH2CH2), 2.68 (s, 4H, –CH2N(CH2CH2)2NCH–),
2.42 (s, 4H, –CH2N(CH2CH2)2NCH–); 13C-NMR
4-(2-fluorophenyl)-9-(2-(4-benzhydrylpiperazin-1-
yl)ethoxy)-7H-furo[3,2-g]chromen-7-one (12f)
Yield 67 %; Yellow solid; m.p. 85–86 °C; Rf = 0.24
(petroleum ether:ethyl acetate = 2:1); IR (KBr): mmax 3150,
3080, 2930, 2808, 1732, 1587, 1462, 1375, 1311, 1150, 1081,
123