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(30 mL per mmol equiv) with stirring. The reaction
mixture was allowed to cool to room temperature, diluted
with CHCl3, and filtered through Celite. The sicciate was
extensively washed with 10% CH3OH in CHCl3. The fil-
trate was concentrated in vacuo and the residue chroma-
tographed on silica gel using chloroform/methanol.
3H), 4.14 (s, 3H), 4.53 (t, 2H, J=7.4), 6.19 (s, 2H), 7.48
(s, 1H), 7.65 (s, 1H), 7.69 (s, 1H), 7.90 (s, 1H), 9.40 (s, 1H);
13C NMR (CDCl3) d 26.9, 45.3, 49.2, 56.3, 56.4, 56.9,
100.8, 101.9, 102.3, 107.1, 108.7, 111.6, 114.9, 119.4, 127.5,
141.0, 143.6, 147.2, 147.7, 149.9, 150.3, 154.1, 164.1;
HRMS calcd for C24H25N3O5H: 436.1872; found
436.1878.
8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethyl-
amino)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (3a).
Prepared from 7a; (41% yield); reaction time 25 min;
mp 283–285 ꢂC (dec.); IR (CHCl3) 1653; 1H NMR
(CDCl3) d 2.33 (s, 6H), 3.04 (t, 2H, J=7.2), 4.07 (s, 3H),
4.14 (s, 3H), 4.64 (t, 2H, J=7.2), 6.18 (s, 2H), 7.47 (s,
1H), 7.68 (s, 1H), 7.89 (s, 2H), 9.37 (s, 1H); 13C NMR
(CDCl3) d 45.9, 49.2, 56.3, 56.3, 57.9, 101.2, 102.0,
102.3, 107.1, 108.8, 111.7, 114.8, 119.3, 127.6, 140.9,
143.5, 147.3, 147.7, 149.9, 150.3, 154.2, 164.1; HRMS
calcd for C23H23N3O5H: 422.1716; found 422.1710.
8,9-Dimethoxy-2,3-methylenedioxy-5-[butyl]-5H-diben-
zo[c,h]1,6-naphthyridin-6-one (3f). Prepared from 7f;
(24% yield); reaction time 45 min; mp 224 ꢂC (dec.); IR
1
(KBr) 1654; H NMR (CDCl3); d 0.99 (t, 3H, J=7.4),
1.62 (m, 2H), 2.09 (m, 2H), 4.07 (s, 3H), 4.14 (s, 3H),
4.49 (m, 2H), 6.19 (s, 2H), 7.50 (s, 1H), 7.61 (s, 1H), 7.70
(s, 1H), 7.92 (s, 1H), 9.40 (s, 1H); 13C NMR (CDCl3) d
13.7, 20.2, 31.2, 50.6, 56.3, 56.4, 100.7, 102.0, 102.2,
107.4, 108.8, 111.7, 114.9, 119.5, 127.4, 141.1, 143.7,
147.1, 147.5, 149.8, 150.3, 154.1, 164.0; HRMS calcd for
C23H22N2O5H: 406.1529; found 406.1534.
8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(N,N-dimethyl-
amino)-1-methylethyl]-5H-dibenzo[c,h]1,6-naphthyridin-
6-one (3b). Prepared froꢂm 7b; (30% yield); reaction
8,9-Dimethoxy-2,3-methylenedioxy-5-(2-tetrahydofura-
nyl)methyl-5H-dibenzo[c,h]1,6-naphthyridin-6-one (3g).
Prepared from 7g; (22% yield); reaction time 30 min;
1
time 30 min; mp 186–187 C; IR (KBr) 1649; H NMR
mp 270–273 ꢂC; IR (CHCl3) 1648; H NMR (CDCl3) d
1
(CDCl3); d 1.95–1.98 (m, 9H), 2.77 (dd, 1H, J=12.0,
8.0), 3.21 (dd, 1H, J=12.0, 8.0), 4.06 (s, 3H), 4.13 (s, 3H),
4.84–4.92 (m, 1H), 6.17 (s, 2H), 7.46 (s, 1H), 7.66 (s, 1H),
7.77 (s, 1H), 7.87 (s, 1H), 9.35 (s, 1H); 13C NMR
(CDCl3) d 19.7, 45.5, 56.2, 56.3, 59.5, 63.1, 100.9, 101.9,
102.1, 107.0, 108.7, 112.4, 115.2, 120.5, 127.3, 142.6,
143.3, 147.0, 147.3, 149.9, 150.1, 154.0, 164.9; HRMS
calcd for C24H25N3O5H: 436.1794; found 436.1863.
1.87 (m, 4H), 3.72 (m, 2H), 4.07 (s, 3H), 4.14 (s, 3H),
4.68 (m, 3H), 6.18 (s, 2H), 7.48 (s, 1H), 7.69 (s, 1H), 7.90
(s, 1H), 8.04 (s, 1H), 9.39 (s, 1H); 13C NMR (CDCl3) d
25.6, 30.3, 54.7, 56.3, 56.4, 68.1, 77.3, 101.7, 102.2,
102.3, 107.0, 109.0, 112.1, 115.2, 119.5, 127.7, 141.2,
143.5, 147.2, 147.4, 149.9, 150.3, 154.2, 164.6; HRMS
calcd for C24H22N2O6H 435.1556; found 435.1566.
8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(pyrrolidin-1-yl)-
ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (3c). Pre-
pared from 7c; (36% yield); reaction time 30 min; mp
8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(hydroxy)ethyl]-
5H-dibenzo[c,h]1,6-naphthyridin-6-one (3h). Prepared
from 9h by treatment with AcOH, THF, H2O (3:1:1) at
room temperature; (84% yield); reaction time 48 h; mp
ꢂ
1
255–257 C (dec.); IR (CHCl3) 1653; H NMR (CDCl3)
d 1.79 (m, 4H), 2.64 (m, 4H), 3.20 (t, 2H, J=7.1), 4.07
(s, 3H), 4.14 (s, 3H), 4.69 (t, 2H, J=7.1), 6.18 (s, 2H),
7.46 (s, 1H), 7.68 (s, 1H), 7.89 (s, 1H), 7.95 (s, 1H), 9.37
(s, 1H); 13C NMR (CDCl3) d 23.7, 49.6, 54.3, 56.3, 56.4,
56.4, 101.3, 102.0, 102.3, 107.0, 108.7, 111.7, 114.8,
119.3, 127.7, 140.9, 143.4, 147.3, 147.8, 150.0, 150.3,
154.2, 164.2; HRMS calcd for C25H25N3O5H: 448.1872;
found 448.1872.
285–286 ꢂC; IR (KBr); 1653, 3448; H NMR (DMSO-
1
d6) d 3.91 (s, 3H), 4.04 (s, 3H), 4.54 (t, 2H, J=4.4), 4.96
(t, 2H, J=4.0), 6.26 (s, 2H), 7.44 (s, 1H), 7.71 (s, 1H),
7.98 (s, 1H), 8.03 (s, 1H), 9.64 (s, 1H); 13C NMR
(DMSO-d6); d 52.6, 56.4, 57.0, 59.5, 101.9, 103.0, 104.0,
106.8, 108.8, 111.9, 114.8, 119.1, 128.0, 141.2, 144.9,
147.4, 147.7, 150.2, 150.5, 154.6, 163.7; HRMS calcd
(M+-OH)for C21H17O5N2 377.1137; found 377.1121.
8,9-Dimethoxy-2,3-methylenedioxy-5-[2-(4-methylpipera-
zin-1-yl)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (3d).
Prepared from 7d; (18% yield); reaction time 25 min;
Compound 9h was prepared from 8h (36% yield); reac-
tion time 30 min; mp 271–273 ꢂC; IR (KBr) 1658; H
1
NMR (CDCl3) d 0.00 (s, 6H), 0.68 (s, 9H), 4.04 (s, 3H),
4.12 (s, 3H), 4.24 (t, 2H, J=8.0), 4.65 (t, 2H, J=8.0),
6.18 (s, 2H), 7.44 (s, 1H), 7.64 (s, 1H), 7.85 (s, 1H), 8.01
(s, 1H), 9.29 (s, 1H); HRMS calcd for C27H33ISiN2O6H:
637.1153; found 637.1212.
ꢂ
1
mp 244–246 C; IR (CHCl3) 1651; H NMR (CDCl3) d
2.27 (s, 3H), 2.51 (m, 8H), 2.95 (t, 2H, J=6.2), 4.07 (s,
3H), 4.15 (s, 3H), 4.69 (t, 2H, J=6.2), 6.19 (s, 2H), 7.48
(s, 1H), 7.70 (s, 1H), 7.91 (s, 2H), 7.92 (s, 1H), 9.39 (s,
1H); 13C NMR (CDCl3) d 29.8, 45.9, 48.6, 53.0, 55.0,
56.4, 56.4, 101.2, 102.0, 102.2, 107.1, 108.9, 112.0, 115.0,
119.5, 127.6, 141.2, 143.4, 147.2, 147.4, 150.0, 150.3,
154.1, 164.4; HRMS calcd for C26H28N4O5H: 477.2138;
found 477.2139.
8,9 - Dimethoxy - 2,3 - methylenedioxy - 5 - [2 - (2 - hydroxy-
ethoxy)ethyl]-5H-dibenzo[c,h]1,6-naphthyridin-6-one (3i).
Prepared from 9i by treatment with AcOH, THF, H2O
(3:1:1) at room temperature; (76% yield); reaction time
18 h; mp 235 ꢂC; IR (KBr) 1654; H NMR (CDCl3) d
1
8,9-Dimethoxy-2,3-methylenedioxy-5-[3-(N,N-dimethyl-
amino)propyl] - 5H - dibenzo[c,h]1,6 - naphthyridin - 6 - one
(3e). Prepared from 7e; (45% yield); reaction time
30 min; mp 262–264 ꢂC (dec.); IR (CHCl3) 1648; 1H
NMR (CDCl3) d 2.29 (m, 8H), 2.45 (m, 2H), 4.07 (s,
3.61 (t, 2H, J=5.2), 3.73 (t, 2H, J=5.2), 4.07 (s, 3H),
4.14 (s, 3H), 4.22 (t, 2H, J=5.6), 4.71 (t, 2H, J=5.6),
6.2 (s, 2H), 7.53 (s, 1H), 7.69 (s, 1H), 7.88 (s, 1H), 8.05
(s, 1H), 9.39 (s, 1H). HRMS calcd for C23H22N2O7H:
439.1506; found 439.1499.