W. Jia et al. / Bioorg. Med. Chem. 17 (2009) 4569–4574
4573
5.24. 8-((Dimethylamino)methyl)-10-methoxy-2,4-dimethyl-
6H-[1]benzothiopyrano[4,3-b]quinolin-9-ol (10e)
5.29. 8-((Diethylamino)methyl)-10-methoxy-2-methyl-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10j)
According to the procedure used to prepare 10a, starting from
compound 9b and dimethylamine, 10e was obtained as yellow
solid. Yield: 61%; mp: 180 °C (dec); MS (ES+) m/z 381.1
(M+H)+; 1H NMR (DMSO-d6, 300 MHz) d: 2.34 (s, 3H), 2.38 (s,
3H), 2.83 (s, 6H), 4.07 (s, 3H), 4.23 (s, 2H), 4.74 (s, 2H), 7.22
(s, 1H), 7.91 (s, 1H), 8.24 (s, 1H), 8.85 (s, 1H); IR (KBr):
1274.9, 1383.9, 1495.5, 1631.5, 2944.8, 3393.1 cmÀ1; Anal. Calcd
for C22H24N2O2S: C, 69.44; H, 6.36; N, 7.36. Found: C, 69.43; H,
6.15; N, 7.08.
According to the procedure used to prepare 10a, starting from
compound 9d and diethylamine, 10j was obtained as yellow solid.
Yield: 67%; mp: 240 °C (dec); MS (ES+) m/z 395.1 (M+H)+; 1H NMR
(DMSO-d6, 300 MHz) d: 1.34 (t, J = 7.2 Hz, 6H), 2.14 (s, 3H), 3.20 (m,
4H), 4.07 (s, 3H), 4.27 (s, 2H), 4.71 (s, 2H), 7.28 (d, J = 7.8 Hz, 1H),
7.41 (d, J = 7.8 Hz, 1H), 7.96 (s, 1H), 8.41 (s, 1H), 8.79 (s, 1H); IR
(KBr): 1280.8, 1383.9, 1492.1, 1543.5, 1632.1, 2592.8, 2925.2,
3419.2 cmÀ1; Anal. Calcd for C23H26N2O2S: C, 70.02; H, 6.64; N,
7.10. Found: C, 68.88; H, 6.59; N, 6.94.
5.25. 10-Methoxy-2,4-dimethyl-8-(morpholinomethyl)-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10f)
5.30. 8-((Dimethylamino)methyl)-10-methoxy-2-methyl-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10k)
According to the procedure used to prepare 10a, starting from
compound 9b and morpholine, 10f was obtained as yellow solid.
Yield: 73%; mp: 246 °C (dec); MS (ES+) m/z 423.2 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 2.30 (s, 3H), 2.35 (s, 3H), 2.54 (m,
4H), 3.58(m, 4H), 3.96 (s, 3H), 4.00 (s, 2H), 4.15 (s, 2H), 7.10 (s,
1H), 7.38 (s, 1H), 8.14 (s, 1H), 8.24 (s, 1H); IR (KBr): 1252.0,
1383.7, 1466.3, 1597.8, 1673.2, 2851.3, 2918.5, 3427.8 cmÀ1; Anal.
Calcd for C24H26N2O3S: C, 68.22; H, 6.20; N, 6.63. Found: C, 68.43;
H, 6.15; N, 6.49.
According to the procedure used to prepare 10a, starting from
compound 9d and dimethylamine, 10k was obtained as yellow
solid. Yield: 81%; mp: 263 °C (dec); MS (ES+) m/z 367.1
(M+H)+; 1H NMR (DMSO-d6, 300 MHz) d: 2.43 (s, 3H), 2.88 (s,
6H), 4.03 (s, 3H), 4.21 (s, 2H), 4.87 (s, 2H), 7.23 (d, J = 7.8 Hz,
1H), 7.34 (d, J = 7.8 Hz, 1H), 7.49 (s, 1H), 8.15 (s, 1H), 8.39 (s,
1H); IR (KBr): 1270.9, 1384.1, 1486.7, 1630.4, 3016.8,
3377.8 cmÀ1; Anal. Calcd for C21H22N2O2S: C, 68.82; H, 6.05; N,
7.64. Found: C, 68.53; H, 5.94; N, 7.45.
5.26. 10-Methoxy-2,4-dimethyl-8-(piperidin-1-ylmethyl)-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10g)
5.31. 10-Methoxy-2-methyl-8-(morpholinomethyl)-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10l)
According to the procedure used to prepare 10a, starting from
compound 9b and piperidine, 10g was obtained as yellow solid.
Yield: 82%; mp: 151 °C (dec); MS (ES+) m/z 421.1 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 1.64–1.79 (m, 6H), 2.34 (s, 3H),
2.38 (s, 3H), 3.10–3.51 (m, 4H), 4.06 (s, 3H), 4.24 (s, 2H), 4.69 (s,
2H), 7.21 (s, 1H), 7.88 (s, 1H), 8.24 (s, 1H), 8.85 (s, 1H); IR (KBr):
1280.0, 1383.3, 1476.4, 1498.6, 1629.2, 2722.0, 3013.6 cmÀ1; Anal.
Calcd for C25H28N2O2S: C, 71.40; H, 6.71; N, 6.66. Found: C, 71.52;
H, 6.48; N, 6.70.
According to the procedure used to prepare 10a, starting from
compound 9d and morpholine, 10l was obtained as yellow solid.
Yield: 62%; mp: 226 °C (dec); MS (ES+) m/z 409.1 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 2.39 (s, 3H), 2.54 (m, 4H), 3.59 (m,
4H), 3.97 (s, 3H), 4.01 (s, 2H), 4.18 (s, 2H), 7.18 (d, J = 7.8 Hz, 1H),
7.31 (d, J = 7.8 Hz, 1H), 7.39 (s, 1H), 8.24 (s, 1H), 8.29 (s, 1H); IR
(KBr): 1284.9, 1384.2, 1497.5, 1544.4, 1630.2, 2942.4, 3385.4 cmÀ1
;
Anal. Calcd for C23H24N2O3S: C, 67.62; H, 5.92; N, 6.86:. Found: C,
67.78; H, 5.88; N, 6.78.
5.27. 2-Fluoro-10-methoxy-8-(pyrrolidin-1-ylmethyl)-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10h)
5.32. 10-Methoxy-2-methyl-8-(pyrrolidin-1-ylmethyl)-6H-
[1]benzothiopyrano[4,3-b]quinolin-9-ol (10m)
According to the procedure used to prepare 10a, starting from
compound 9c and pyrrolidine, 10h was obtained as yellow solid.
Yield: 78%; mp: 197 °C (dec); MS (ES+) m/z 397.0 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 1.88–2.08 (m, 4H), 3.24–3.48 (m,
4H), 4.07 (s, 3H), 4.28 (s, 2H), 4.78 (s, 2H), 7.25–7.31 (m, 1H),
7.49–7.35 (m, 1H), 7.68 (s, 1H), 8.22–8.26 (m, 1H), 8.72 (s, 1H);
IR (KBr): 1240.2, 1384.3, 1464.4, 1480.7, 1601.9, 2838.7, 2965.0,
3419.9 cmÀ1; Anal. Calcd for C22H21FN2O2S: C, 66.65; H, 5.34; N,
7.07. Found: C, 66.49; H, 5.49; N, 7.10.
According to the procedure used to prepare 10a, starting from
compound 9d and pyrrolidine, 10m was obtained as yellow solid.
Yield: 79%; mp: 190 °C (dec); MS (ES+) m/z 393.2 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 2.00 (m, 4H), 2.40 (s, 3H), 3.24–
3.48 (m, 4H), 4.06 (s, 3H), 4.28 (s, 2H), 4.77 (s, 2H), 7.15 (d,
J = 7.8 Hz, 1H), 7.31 (d, J = 7.8 Hz, 1H), 7.42 (s, 1H), 8.20 (s, 1H),
8.29 (s, 1H); IR (KBr): 1258.5, 1384.2, 1472.0, 1621.4, 3422.1 cmÀ1
;
Anal. Calcd for C23H24N2O2S: C, 70.38; H, 6.16; N, 7.14. Found: C,
70.20; H, 6.00; N, 7.26.
5.28. 10-Methoxy-2-methyl-8-((4-methylpiperazin-1-
5.33. 3-Fluoro-10-methoxy-8-((4-methylpiperazin-1-
yl)methyl)-6H-[1]benzothiopyrano[4,3-b]quinolin-9-ol (10i)
yl)methyl)-6H-[1]benzothiopyrano[4,3-b]quinolin-9-ol (10n)
According to the procedure used to prepare 10a, starting from
compound 9d and 1-methylpiperazine, 10i was obtained as yellow
solid. Yield: 57%; mp: 215 °C (dec); MS (ES+) m/z 422.2 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 2.39 (m, 4H), 2.41 (s, 3H) 2.59 (m,
4H), 3.17 (s, 3H), 3.96 (s, 3H), 4.07 (s, 2H), 4.21 (s, 2H), 7.17 (d,
J = 7.8 Hz, 1H), 7.31 (d, J = 7.8 Hz, 1H), 7.41 (s, 1H), 8.23 (s, 1H),
According to the procedure used to prepare 10a, starting from
compound 9e and 1-methylpiperazine, 10n was obtained as yellow
solid. Yield: 54%; mp: 235 °C (dec); MS (ES+) m/z 426.1 (M+H)+; 1H
NMR (DMSO-d6, 300 MHz) d: 2.17 (s, 3H), 2.38 (m, 4H), 2.57 (m,
4H), 3.95 (s, 3H), 4.09 (s, 2H), 4.25 (s, 2H), 7.08–7.22 (m, 2H),
7.34 (s, 1H), 8.23 (s, 1H), 8.41–8.51 (m, 1H); IR (KBr): 1266.5,
1382.7, 1476.6, 1621.4, 22966.4, 3422.1 cmÀ1; Anal. Calcd for
C23H24FN3O2S: C, 64.92; H, 5.68; N, 9.88. Found: C, 64.88; H,
5.49; N, 9.80.
8.28 (s, 1H); IR (KBr): 1232.1, 1384.2, 1591.9, 2936.5, 3428.2 cmÀ1
;
Anal. Calcd for C24H27N3O2S: C, 68.38; H, 6.46; N, 9.97. Found: C,
68.50; H, 6.49; N, 9.84.