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PATEL ET AL.
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103.5, 98.7, 91.4, 69.1, 57.2, 54.5, 34.1, 28.8, 26.8. Anal. calcd. for
C29H29ClN2O6S: C, 61.21; H, 5.14; N, 4.92. Found: C, 61.11; H, 5.01;
N, 4.99.
CH2), 3.46 (t, J = 6.56 Hz, 2H), 2.80 (t, J = 4.87 Hz, 4H, CH2),
2.19–2.08 (m, 2H), 2.04–1.99 (m, 2H); 13C NMR (DMSO‐d6,
100 MHz): δ 183.3, 166.9, 165.1, 163.7, 158.9, 143.6–127.1, 107.2,
104.3, 99.1, 95.4, 67.2, 57.4, 51.9, 35.6, 29.1, 27.8. Anal. calcd. for
C29H29FN2O6S: C, 63.03; H, 5.29; N, 5.07. Found: C, 63.21; H, 5.13;
N, 4.96.
7‐(4‐(4‐(2,4‐Dichlorophenylsulfonyl)piperazin‐1‐yl)‐
butoxy)‐5‐hydroxy‐2‐phenyl‐4H‐chromen‐4‐one (7c)
Yield: 63%. m.p. 253–255°C; IR (KBr) cm−1: 3,072; 2,933; 2,920;
2,870; 1,661; 1,633; 1,573; 1,372; 1,346; 1,244; 1,166; 1,141; 1,044.
1H NMR (DMSO‐d6, 400 MHz): δ 12.75 (s, 1H), 7.91–7.79 (m, 3H),
7.66–7.48 (m, 5H), 6.71 (s, 1H), 6.44 (d, J = 2.35 Hz, 1H), 6.18
(d, J = 2.27 Hz, 1H), 4.27 (t, J = 6.06 Hz, 2H), 3.50 (t, J = 4.88 Hz, 4H,
CH2), 3.42 (t, J = 6.53 Hz, 2H), 2.85 (t, J = 4.89 Hz, 4H, CH2),
2.19–2.09 (m, 2H), 2.04–1.99 (m, 2H); 13C NMR (DMSO‐d6,
100 MHz): δ 183.2, 169.7, 164.7, 160.9, 158.2, 137.9–121.7, 107.6,
103.3, 98.9, 93.0, 69.1, 57.5, 52.8, 33.3, 28.6, 27.0. Anal. calcd. for
C29H28Cl2N2O6S: C, 57.71; H, 4.68; N, 4.64. Found: C, 57.88; H, 4.79;
N, 4.50.
7‐(4‐(4‐(2,4‐Difluorophenylsulfonyl)piperazin‐1‐yl)‐
butoxy)‐5‐hydroxy‐2‐phenyl‐4H‐chromen‐4‐one (7g)
Yield: 58%. m.p. 253–255°C; IR (KBr) cm−1: 3,071; 2,937; 2,937; 2,872;
1,655; 1,626; 1,579; 1,377; 1,351; 1,257; 1,159; 1,137; 1,036. 1H NMR
(DMSO‐d6, 400 MHz): δ 12.74 (s, 1H), 7.92–7.87 (m, 2H), 7.74–7.60 (m,
6H), 6.69 (s, 1H), 6.38 (d, J = 2.32 Hz, 1H), 6.19 (d, J = 2.25 Hz, 1H), 4.22
(t, J = 6.07 Hz, 2H), 3.61 (t, J = 4.83 Hz, 4H, CH2), 3.41 (t, J = 6.50 Hz,
2H), 2.86 (t, J = 4.96 Hz, 4H, CH2), 2.15–2.06 (m, 2H), 2.02–1.96 (m,
2H); 13C NMR (DMSO‐d6, 100 MHz): δ 181.9, 166.1, 162.5, 161.1,
159.3, 139.6–125.9, 108.1, 104.5, 98.9, 93.0, 68.5, 58.5, 53.6, 33.6,
28.9, 26.4. Anal. calcd. for C29H28F2N2O6S: C, 61.04; H, 4.95; N, 4.91.
Found: C, 61.21; H, 5.12; N, 4.99.
7‐(4‐(4‐(4‐Bromophenylsulfonyl)piperazin‐1‐yl)‐
butoxy)‐5‐hydroxy‐2‐phenyl‐4H‐chromen‐4‐one (7d)
Yield: 69%. m.p. 253–255°C; IR (KBr) cm−1: 3,076; 2,944; 2,933;
2,881; 1,669; 1,625; 1,586; 1,369; 1,340; 1,250; 1,157; 1,139; 1,036.
1H NMR (DMSO‐d6, 400 MHz): δ 12.79 (s, 1H), 7.93–7.87 (m, 2H),
7.75–7.54 (m, 7H), 6.79 (s, 1H), 6.39 (d, J = 2.30 Hz, 1H), 6.10
(d, J = 2.21 Hz, 1H), 4.19 (t, J = 6.13 Hz, 2H), 3.59 (t, J = 4.84 Hz, 4H,
CH2), 3.49 (t, J = 6.55 Hz, 2H), 2.81 (t, J = 4.96 Hz, 4H, CH2),
2.15–2.08 (m, 2H), 2.03–1.97 (m, 2H); 13C NMR (DMSO‐d6,
100 MHz): δ 181.0, 166.8, 162.7, 160.7, 159.1, 137.6–126.3, 106.9,
101.3, 99.4, 93.4, 66.8, 58.7, 52.6, 33.8, 28.8, 27.3. Anal. calcd. for
C29H29BrN2O6S: C, 56.77; H, 4.76; N, 4.57. Found: C, 56.71; H, 4.89;
N, 4.69.
5‐Hydroxy‐2‐phenyl‐7‐(4‐(4‐(4‐(trifluoromethoxy)phenylsulfonyl)‐
piperazin‐1‐yl)butoxy)‐4H‐chromen‐4‐one (7h)
Yield: 62%. m.p. 253–255°C; IR (KBr) cm−1: 3,079; 2,940; 2,934;
2,869; 1,659; 1,617; 1,573; 1,371; 1,348; 1,249; 1,167; 1,144; 1,041.
1H NMR (DMSO‐d6, 400 MHz): δ 12.70 (s, 1H), 7.89–7.83 (m, 2H),
7.69–7.37 (m, 7H), 6.78 (s, 1H), 6.47 (d, J = 2.39 Hz, 1H), 6.09
(d, J = 2.22 Hz, 1H), 4.21 (t, J = 6.15 Hz, 2H), 3.55 (t, J = 4.89 Hz, 4H,
CH2), 3.45 (t, J = 6.57 Hz, 2H), 2.82 (t, J = 4.93 Hz, 4H, CH2),
2.16–2.05 (m, 2H), 2.03–1.99 (m, 2H); 13C NMR (DMSO‐d6,
100 MHz): δ 182.6, 168.2, 164.7, 163.1, 158.9, 136.6–124.5, 106.2,
103.3, 97.2, 94.5, 70.2, 59.9, 55.2, 35.7, 29.5, 27.2. Anal. calcd. for
C30H29F3N2O7S: C, 58.25; H, 4.73; N, 4.53. Found: C, 58.13; H, 4.90;
N, 4.66.
7‐(4‐(4‐(2,4‐Dibromophenylsulfonyl)piperazin‐1‐yl)butoxy)‐5‐hydro-
xy‐2‐phenyl‐4H‐chromen‐4‐one (7e)
Yield: 57%. m.p. 253–255°C; IR (KBr) cm−1: 3,070; 2,948; 2,921;
2,864; 1,658; 1,617; 1,577; 1,380; 1,343; 1,255; 1,169; 1,152; 1,027.
1H NMR (DMSO‐d6, 400 MHz): δ 12.71 (s, 1H), 7.94–7.89 (m, 2H),
7.79–7.68 (m, 6H), 6.70 (s, 1H), 6.48 (d, J = 2.37 Hz, 1H), 6.17
(d, J = 2.28 Hz, 1H), 4.29 (t, J = 6.16 Hz, 2H), 3.55 (t, J = 4.82 Hz, 4H,
CH2), 3.40 (t, J = 6.54 Hz, 2H), 2.87 (t, J = 4.90 Hz, 4H, CH2),
2.14–2.02 (m, 2H), 2.01–1.96 (m, 2H); 13C NMR (DMSO‐d6,
100 MHz): δ 182.5, 167.6, 163.1, 162.6, 159.1, 138.9–123.1, 109.6,
104.2, 96.8, 91.9, 68.6, 58.1, 54.4, 31.9, 27.8, 26.3. Anal. calcd. for
C29H28Br2N2O6S: C, 50.30; H, 4.08; N, 4.05. Found: C, 50.14; H, 4.22;
N, 4.34.
5‐Hydroxy‐7‐(4‐(4‐(4‐nitrophenylsulfonyl)piperazin‐1‐yl)‐
butoxy)‐2‐phenyl‐4H‐chromen‐4‐one (7i)
Yield: 65%. m.p. 253–255°C; IR (KBr) cm−1: 3,080; 2,933; 2,922; 2,878;
1,669; 1,629; 1,589; 1,379; 1,335; 1,254; 1,171; 1,150; 1,029. 1H NMR
(DMSO‐d6, 400 MHz): δ 12.73 (s, 1H), 7.93–7.87 (m, 2H), 7.79–7.53 (m,
7H), 6.72 (s, 1H), 6.40 (d, J = 2.35 Hz, 1H), 6.17 (d, J = 2.26 Hz, 1H), 4.25
(t, J = 6.15 Hz, 2H), 3.57 (t, J = 4.80 Hz, 4H, CH2), 3.39 (t, J = 6.51 Hz,
2H), 2.84 (t, J = 4.90 Hz, 4H, CH2), 2.17–2.08 (m, 2H), 2.00–1.95 (m,
2H); 13C NMR (DMSO‐d6, 100 MHz): δ 180.9, 165.7, 162.1, 161.6,
159.2, 138.0–125.2, 109.2, 104.2, 98.9, 92.9, 68.2, 56.8, 51.9, 33.3,
28.1, 27.2. Anal. calcd. for C29H29N3O8S: C, 60.09; H, 5.04; N, 7.25.
Found: C, 60.19; H, 5.23; N, 7.14.
7‐(4‐(4‐(4‐Fluorophenylsulfonyl)piperazin‐1‐yl)‐
butoxy)‐5‐hydroxy‐2‐phenyl‐4H‐chromen‐4‐one (7f)
5‐Hydroxy‐7‐(4‐(4‐(4‐methoxyphenylsulfonyl)piperazin‐1‐yl)butoxy)‐
2‐phenyl‐4H‐chromen‐4‐one (7j)
Yield: 71%. m.p. 253–255°C; IR (KBr) cm−1: 3,069; 2,944; 2,929; 2,872;
1,671; 1,622; 1,574; 1,381; 1,346; 1,244; 1,166; 1,145; 1,031. 1H NMR
(DMSO‐d6, 400 MHz): δ 12.78 (s, 1H), 7.91–7.85 (m, 2H), 7.68–7.36 (m,
7H), 6.68 (s, 1H), 6.37 (d, J = 2.31 Hz, 1H), 6.15 (d, J = 2.26 Hz, 1H), 4.20
Yield: 49%. m.p. 253–255°C; IR (KBr) cm−1: 3,084; 2,942; 2,924;
2,874; 1,660; 1,630; 1,581; 1,388; 1,337; 1,242; 1,162; 1,147; 1,033.
1H NMR (DMSO‐d6, 400 MHz): δ 12.77 (s, 1H), 7.90–7.82 (m, 2H),
7.70–7.39 (m, 7H), 6.68 (s, 1H), 6.40 (d, J = 2.33 Hz, 1H), 6.12
(d, J = 2.24 Hz, 1H), 4.27 (t, J = 6.11 Hz, 2H), 3.59 (t, J = 4.86 Hz, 4H,