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2H); 4.87 (s, 2H); 7.27–7.42 (m, 5H); EIMS m/z 301 (M+). Anal.
Calcd for C18H23NO3: C, 71.73; H, 7.69; N, 4.65. Found: C, 72.45;
H, 7.67; N, 4.66.
1H); 7.50 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H); 7.54 (d, J = 1.8 Hz, 1H);
EIMS m/z 347 (M+). Anal. Calcd for C19H25NO5: C, 65.69; H, 7.25;
N, 4.03. Found: C, 65.60; H, 7.27; N, 4.04.
4.5.4.4. 3-Phenyl-4-(2-(piperidin-1-yl)ethoxy)furan-2(5H)-one
(9).
4.5.4.12. 3-(3,4-Dimethoxyphenyl)-4-(2-(4-methylpiperazin-1-
Light yellow oil, 54%, 1H NMR (CDCl3): 1.40–1.50 (m,
yl)ethoxy)furan-2(5H)-one (17).
Colorless crystal, 64%, mp
2H); 1.51–1.68 (m, 4H); 2.40–2.49 (m, 4H); 2.72 (t, J = 5.7 Hz,
2H); 4.22 (t, J = 5.5 Hz, 2H); 4.88 (s, 2H); 7.29 (d, J = 7.4 Hz, 1H);
7.38 (t, J = 7.1 Hz, 2H); 7.86 (dd, J = 8.6 Hz, J = 1.4 Hz, 2H); EIMS
m/z 287 (M+). Anal. Calcd for C17H21NO3: C, 71.06; H, 7.37; N,
4.87. Found: C, 71.82; H, 7.35; N, 4.86.
69–71 °C, 1H NMR (DMSO-d6): 2.16 (s, 3H); 2.23–2.38 (m, 4H);
2.42–2.55 (m, 4H); 2.73 (t, J = 5.3 Hz, 2H); 3.75 (s, 3H); 3.76 (s,
3H); 4.34 (t, J = 5.4 Hz, 2H); 5.11 (s, 2H); 6.97 (d, J = 8.4 Hz, 1H);
7.49 (d, J = 2.0 Hz, 1H); 7.53 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H); EIMS
m/z 362 (M+). Anal. Calcd for C19H26N2O5: C, 62.97; H, 7.23; N,
7.73. Found: C, 62.88; H, 7.25; N, 7.74.
4.5.4.5. 3-Phenyl-4-(2-(pyrrolidin-1-yl)ethoxy)furan-2(5H)-one
(10).
Colorless crystal, 75%, mp 81–82 °C, 1H NMR (CDCl3):
4.5.4.13.
yl)ethoxy)furan-2(5H)-one (18).
3-(3,4-Dichlorophenyl)-4-(2-(4-methylpiperazin-1-
White powder, 65%, mp
1.77–1.86 (m, 4H); 2.51–2.63 (m, 4H); 2.90 (t, J = 5.9 Hz, 2H);
4.23 (t, J = 5.9 Hz, 2H); 4.87 (s, 2H); 7.30 (d, J = 6.3 Hz, 1H); 7.38
(t, J = 7.1 Hz, 2H); 7.84 (d, J = 7.1 Hz, 2H); EIMS m/z 273 (M+). Anal.
Calcd for C16H19NO3: C, 70.31; H, 7.01; N, 5.12. Found: C, 70.40; H,
6.99; N, 5.11.
92–94 °C, 1H NMR (DMSO-d6): 2.15 (s, 3H); 2.23–2.37 (m, 4H);
2.41–2.53 (m, 4H); 2.74 (t, J = 5.3 Hz, 2H); 4.34 (t, J = 5.4 Hz, 2H);
5.10 (s, 2H); 7.18 (d, J = 8.0 Hz, 1H); 7.28 (s, 1H); 7.43 (d, J = 8.1 Hz,
1H); EIMS m/z 370 (M+). Anal. Calcd for C17H20Cl2N2O3: C, 55.00;
H, 5.43; Cl, 19.10; N, 7.55. Found: C, 55.09; H, 5.43; Cl, 19.07; N, 7.54.
4.5.4.6.
(11).
4-(2-Morpholinoethoxy)-3-phenylfuran-2(5H)-one
Colorless crystal, 63%, mp 118–119 °C, 1H NMR
4.5.4.14.
oxy)furan-2(5H)-one (19).
3-(3,4-Difluorophenyl)-4-(2-(piperidin-1-yl)eth-
White powder, 43%, mp 119–
(DMSO-d6): 2.48 (t, J = 5.3 Hz, 4H); 2.74 (t, J = 5.5 Hz, 2H); 3.58 (t,
J = 5.3 Hz, 4H); 4.37 (t, J = 5.5 Hz, 2H); 5.15 (s, 2H); 7.27 (d,
J = 8.3 Hz, 1H); 7.39 (t, J = 8.3 Hz, 2H); 7.88 (d, J = 8.3 Hz, 2H); EIMS
m/z 289 (M+). Anal. Calcd for C16H19NO4: C, 66.42; H, 6.62; N, 4.84.
Found: C, 66.33; H, 6.64; N, 4.83.
121 °C, 1H NMR (CDCl3): 1.39–1.50 (m, 2H); 1.52–1.67 (m, 4H);
2.47 (t, J = 5.0 Hz, 4H); 2.75 (t, J = 5.4 Hz, 2H); 4.24 (t, J = 5.5 Hz,
2H); 4.89 (s, 2H); 7.32 (d, J = 8.8 Hz, 1H); 7.58 (d, J = 8.7 Hz, 1H);
7.65 (t, J = 8.8 Hz, 1H); EIMS m/z 323 (M+). Anal. Calcd for
C17H19F2NO3: C, 63.15; H, 5.92; F, 11.75; N, 4.33. Found: C, 63.07;
4.5.4.7.
2(5H)-one (12).
4-(2-(4-Methylpiperazin-1-yl)ethoxy)-3-phenylfuran-
Colorless crystal, 85%, mp 45–46 °C, 1H
H, 5.93; F, 11.77; N, 4.33.
NMR (CDCl3): 2.30 (s, 3H); 2.40–2.49 (m, 4H); 2.51–2.63 (m, 4H);
2.78 (t, J = 5.5 Hz, 2H); 4.22 (t, J = 5.5 Hz, 2H); 4.87 (s, 2H); 7.30
(d, J = 7.3 Hz, 1H); 7.38 (t, J = 7.1 Hz, 2H); 7.84 (dd, J = 8.0 Hz,
J = 1.5 Hz, 2H); EIMS m/z 302 (M+). Anal. Calcd for C17H22N2O3: C,
67.53; H, 7.33; N, 9.26. Found: C, 67.46; H, 7.32; N, 9.28.
4.5.4.15.
2(5H)-one (20).
3-(3-Chlorophenyl)-4-(2-morpholinoethoxy)furan-
Colorless crystal, 63%, mp 131–133 °C, 1H
NMR (DMSO-d6): 2.48 (t, J = 5.3 Hz, 4H); 2.75 (t, J = 5.5 Hz, 2H);
3.57 (t, J = 5.3 Hz, 4H); 4.37 (t, J = 5.5 Hz, 2H); 5.15 (s, 2H); 7.10–
7.22 (m, 3H); 7.26 (d, J = 8.5 Hz, 1H); EIMS m/z 323 (M+). Anal.
Calcd for C16H18ClNO4: C, 59.35; H, 5.60; Cl, 10.95; N, 4.33. Found:
C, 59.42; H, 5.59; Cl, 10.93; N, 4.33.
4.5.4.8.
(13).
4-(2-(Benzylamino)ethoxy)-3-phenylfuran-2(5H)-one
Colorless crystal, 37%, mp 110–112 °C, 1H NMR (CDCl3):
3.27 (t, J = 5.3 Hz, 2H); 3.59 (t, J = 5.3 Hz, 2H); 4.41 (s, 2H); 4.91 (s,
2H); 7.06 (d, J = 6.4 Hz, 2H); 7.20–7.35 (m, 8H); EIMS m/z 309 (M+).
Anal. Calcd for C19H19NO3: C, 73.77; H, 6.19; N, 4.53. Found: C,
73.84; H, 6.17; N, 4.54.
4.5.4.16.
2(5H)-one (21).
3-(3-Bromophenyl)-4-(2-morpholinoethoxy)furan-
Colorless crystal, 54%, mp 136–138 °C, 1H
NMR (DMSO-d6): 2.48 (t, J = 5.4 Hz, 4H); 2.75 (t, J = 5.5 Hz, 2H);
3.58 (t, J = 5.3 Hz, 4H); 4.39 (t, J = 5.5 Hz, 2H); 5.15 (s, 2H); 7.22
(t, J = 8.4 Hz, 1H); 7.33 (d, J = 8.4 Hz, 1H); 7.37 (d, J = 8.2 Hz, 1H);
7.44 (s, 1H); EIMS m/z 367 (M+). Anal. Calcd for C16H18BrNO4: C,
52.19; H, 4.93; Br, 21.70; N, 3.80. Found: C, 52.25; H, 4.94; Br,
21.68; N, 3.79.
4.5.4.9. 4-(2-(2-(4-Nitrophenyl)hydrazinyl)ethoxy)-3-phenylfu-
ran-2(5H)-one (14).
Yellow crystal, 78%, mp 259–261 °C, 1H
NMR (DMSO-d6): 3.89 (t, J = 5.5 Hz, 2H); 4.60 (t, J = 5.3 Hz, 2H);
5.16 (s, 2H); 7.28 (t, J = 7.5 Hz, 1H); 7.41 (t, J = 7.7 Hz, 2H); 7.91
(dd, J = 8.4 Hz, J = 1.3 Hz, 2H); 8.10 (d, J = 9.0 Hz, 2H); 8.26 (d,
J = 8.9 Hz, 2H); EIMS m/z 355 (M+). Anal. Calcd for C18H17N3O5: C,
60.84; H, 4.82; N, 11.83. Found: C, 60.89; H, 4.81; N, 11.84.
4.5.4.17. 3-(3-Methoxyphenyl)-4-(2-morpholinoethoxy)furan-
2(5H)-one (22).
Colorless crystal, 63%, mp 125–126 °C, 1H
NMR (DMSO-d6): 2.48 (t, J = 5.4 Hz, 4H); 2.74 (t, J = 5.5 Hz, 2H);
3.58 (t, J = 5.3 Hz, 4H); 3.71 (s, 3H); 4.37 (t, J = 5.5 Hz, 2H); 5.15
(s, 2H); 7.12–7.24 (m, 3H); 7.26 (d, J = 8.5 Hz, 1H); EIMS m/z 319
(M+). Anal. Calcd for C17H21NO5: C, 46.98; H, 2.71; Br, 39.07; N,
3.42. Found: C, 46.91; H, 2.71; Br, 39.12; N, 3.42.
4.5.4.10.
phenyl)furan-2(5H)-one (15).
4-(2-(Cyclohexylamino)ethoxy)-3-(3,4-dimethoxy-
Colorless crystal, 68%, mp
137–139 °C, 1H NMR (CDCl3): 0.80–1.02 (m, 3H); 1.23–1.42 (m,
3H); 1.60–1.74 (m, 4H); 1.93 (b s, 1H); 3.23 (t, J = 6.4 Hz, 2H);
3.32–3.43 (m, 1H); 3.54 (t, J = 6.3 Hz, 2H); 3.85 (s, 3H); 3.89 (s,
3H); 4.88 (s, 2H); 6.80 (d, J = 1.8 Hz, 1H); 6.81 (dd, J = 8.0 Hz,
J = 1.8 Hz, 1H); 6.86 (d, J = 8.3 Hz, 1H); EIMS m/z 361 (M+). Anal.
Calcd for C20H27NO5: C, 66.46; H, 7.53; N, 3.88. Found: C, 66.51;
H, 7.51; N, 3.87.
4.5.4.18.
2(5H)-one (23).
3-(4-Chlorophenyl)-4-(2-morpholinoethoxy)furan-
White powder, 51%, mp 124–126 °C, 1H
NMR (DMSO-d6): 2.48 (t, J = 5.3 Hz, 4H); 2.74 (t, J = 5.5 Hz, 2H);
3.58 (t, J = 5.3 Hz, 4H); 4.38 (t, J = 5.5 Hz, 2H); 5.15 (s, 2H); 7.50
(d, J = 8.5 Hz, 2H); 7.59 (d, J = 8.5 Hz, 2H); EIMS m/z 323 (M+). Anal.
Calcd for C16H18ClNO4: C, 59.35; H, 5.60; Cl, 10.95; N, 4.33. Found:
C, 59.43; H, 5.59; Cl, 10.93; N, 4.34.
4.5.4.11.
3-(3,4-Dimethoxyphenyl)-4-(2-(piperidin-1-yl)eth-
oxy)furan-2(5H)-one (16).
Colorless crystal, 89%, mp 116–
117 °C, 1H NMR (CDCl3): 1.38–1.49 (m, 2H); 1.51–1.67 (m, 4H);
2.46 (t, J = 5.0 Hz, 4H); 2.73 (t, J = 5.5 Hz, 2H); 3.90 (s, 3H); 3.91
(s, 3H); 4.22 (t, J = 5.5 Hz, 2H); 4.87 (s, 2H); 6.89 (d, J = 8.4 Hz,
4.5.4.19.
2(5H)-one (24).
(t, J = 5.3 Hz, 4H); 2.75 (t, J = 5.5 Hz, 2H); 3.58 (t, J = 5.4 Hz, 4H);
3-(4-Bromophenyl)-4-(2-morpholinoethoxy)furan-
Colorless oil, 67%, 1H NMR (DMSO-d6): 2.48