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X. Xiao et al. / Bioorg. Med. Chem. 12 (2004) 5147–5160
4.4. 11-(60-Aminohexylidene)-5,6-dihydro-2,3-dimethoxy-
6-methyl-8,9-methylenedioxy-5-oxo-11H-indeno[1,2-c]iso-
quinoline (8)
yielding a yellow powder (55mg, 48%): mp 216–
218ꢁC. H NMR (500MHz, DMSO-d6) d 7.69 (s, 1H),
1
7.64 (s, 1H), 7.54 (s, 1H), 7.51 (s, 1H), 6.95 (t,
J = 6.1Hz, 1H), 6.15 (s, 2H), 3.99 (s, 3H), 3.96 (s, 3H),
3.87 (s, 3H), 3.21 (t, J = 7.0Hz, 2H), 3.13 (q,
J = 6.6Hz, 2H), 2.60 (s, 3H). ESIMS m/z (rel. inten-
Prepared from 2 (100mg, 0.27mmol) and 19 (71mg,
0.33mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH (5:1),
yielding a yellow powder (54mg, 45%): mp > 245ꢁC
(dec). 1H NMR (300MHz, DMSO-d6) d 7.82 (br
s, 2H), 7.68 (s, 1H), 7.61 (s, 1H), 7.49 (s, 1H), 7.42 (s,
1H), 6.98 (t, J = 6.1Hz, 1H), 6.13 (s, 2H), 3.96 (s, 3H),
3.95 (s, 3H), 3.87 (s, 3H), 2.78–2.86 (m, 4H), 1.58–1.73
(m, 4H), 1.45–1.57 (m, 2H); ESIMS m/z (rel. intensity)
449 (100, MH+). Anal. Calcd for C26H28N2O5Æ
0.85CHCl3: C, 58.64; H, 5.29; N, 5.09. Found: C,
58.32; H, 5.73; N, 5.09.
sity)
421
(100,
MH+).
Anal.
Calcd
for
C24H24N2O5Æ0.55CHCl3: C, 60.66; H, 5.09; N, 5.76.
Found: C, 60.99; H, 5.56; N, 5.15.
4.8. 11-(40-Methylaminobutylidene)-5,6-dihydro-2,3-
dimethoxy-6-methyl-8,9-methylenedioxy-5-oxo-11H-
indeno[1,2-c]isoquinoline (12)
Prepared from 2 (100mg, 0.27mmol) and 41 (66mg,
0.33mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3 and CHCl3–
MeOH (6:1), yielding a yellow powder (57mg, 48%):
4.5. 11-(40-Phthalylaminobutylidene)-5,6-dihydro-2,3-
dimethoxy-6-methyl-8,9-methylenedioxy-5-oxo-11H-
indeno[1,2-c]isoquinoline (9)
1
mp > 215ꢁC (dec). H NMR (300MHz, DMSO-d6) d
7.70 (s, 1H), 7.64 (s, 1H), 7.58 (s, 1H), 7.52 (s, 1H),
6.91 (t, J = 6.1Hz, 1H), 6.15 (s, 2H), 4.00 (s, 3H), 3.97
(s, 3H), 3.87 (s, 3H), 3.07 (t, J = 6.0Hz, 2H), 2.89–2.94
(m, 2H), 2.58 (s, 3H), 1.95–2.05 (m, 2H); ESIMS m/z
(rel. intensity) 435 (100, MH+). Anal. Calcd for
C25H26N2O5Æ1.4H2O: C, 65.32; H, 6.32; N, 6.09. Found:
C, 65.01; H, 6.21; N, 5.81.
Prepared from 2 (300mg, 0.82mmol) and 24 (214mg,
0.99mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH
(20:1), yielding a yellow powder (202mg, 44%): mp
262–264ꢁC. 1H NMR (300MHz, CDCl3) d 7.83 (s,
1H), 7.63–7.66 (m, 2H), 7.55–7.57 (m, 2H), 7.42 (s,
1H), 7.37 (s, 1H), 7.28 (s, 1H), 6.87 (t, J = 6.3Hz, 1H),
6.04 (s, 2H), 4.08 (s, 3H), 4.01 (s, 3H), 4.00 (s, 3H),
3.85 (t, J = 6.6Hz, 2H), 2.91 (q, J = 6.6Hz, 2H), 2.12
(quin, J = 6.6Hz, 2H); IR (film) 3460, 2938, 1769,
1709, 1634, 1611, 1517, 1484, 1396, 1253, 1030,
722cmꢀ1; ESIMS m/z (rel. intensity) 551 (100, MH+).
Anal. Calcd for C32H26N2O7Æ0.4H2O: C, 68.91; H,
4.86; N, 5.02. Found: C, 68.91; H, 4.88; N, 5.13.
4.9. 11-[20-N-(30-Aminopropyl)-aminoethylidene)-5,6-di-
hydro-2,3-dimethoxy-6-methyl-8,9-methylenedioxy-5-
oxo-11H-indeno[1,2-c]isoquinoline (13)
Prepared from 2 (100mg, 0.27mmol) and 35 (104mg,
0.33mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH–
NH3Æ H2O (100:20:2.0), yielding a yellow powder
(30mg, 24%): mp 183–185ꢁC. 1H NMR (300MHz,
DMSO-d6) d 7.69 (s, 1H), 7.62 (s, 1H), 7.53 (s, 1H),
7.03 (s, 1H), 7.03 (t, J = 6.1Hz, 1H), 6.13 (s, 2H), 3.96
(s, 6H), 3.89 (s, 3H), 2.83–2.89 (m, 2H), 2.65–2.75 (m,
4H), 1.52–1.62 (m, 2H); ESIMS m/z (rel. intensity) 450
(100, MH+). Anal. Calcd for C25H27N3O5Æ0.5CHCl3:
C, 60.15; H, 5.44; N, 8.25. Found: C, 60.08; H, 5.37;
N, 8.23.
4.6. 11-(50-Phthalylaminopentylidene)-5,6-dihydro-2,3-
dimethoxy-6-methyl-8,9-methylenedioxy-5-oxo-11H-
indeno[1,2-c]isoquinoline (10)
Prepared from 2 (300mg, 0.82mmol) and 25 (229mg,
0.99mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH
(20:1) yielding a yellow powder (210mg, 45%): mp
205–207ꢁC. 1H NMR (300MHz, CDCl3) d 7.88 (s,
1H), 7.79–7.82 (m, 2H), 7.66–7.71(m, 2H), 7.45 (s,
1H), 7.40 (s, 1H), 7.33 (s, 1H), 6.86 (t, J = 7.2Hz, 1H),
6.04 (s, 2H), 4.04 (s, 3H), 4.02 (s, 3H), 4.00 (s, 3H),
3.77 (t, J = 7.2Hz, 2H), 2.88 (t, J = 7.2Hz, 2H), 1.91
(quin, J = 7.2Hz, 2H), 1.77 (quin, J = 7.2Hz, 2H);
ESIMS m/z (rel. intensity) 565 (100, MH+). Anal. Calcd
for C33H28N2O7: C, 70.20; H, 4.80; N, 4.96. Found: C,
69.88; H, 4.98; N, 4.90.
4.10. 11-[30-N-(30-Aminopropyl)-aminopropylidene]-5,6-
dihydro-2,3-dimethoxy-6-methyl-8,9-methylenedioxy-5-
oxo-11H-indeno[1,2-c]isoquinoline (14)
Prepared from 2 (100mg, 0.27mmol) and 38 (132mg,
0.4mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH–
NH3Æ H2O (100:20:2), affording a yellow solid powder
1
(45mg, 36%): mp > 210ꢁC (dec.). H NMR (300MHz,
DMSO-d6) d 7.71 (s, 1H), 7.65 (s, 1H), 7.57 (s, 1H),
7.52 (s, 1H), 7.04 (t, J = 6.0Hz, 1H), 6.15 (s, 2H), 4.01
(s, 3H), 3.98 (s, 3H), 3.88 (s, 3H), 3.08–3.12 (m, 4H),
2.85–2.91 (m, 4H), 1.87–1.90 (m, 2H). ESIMS m/z (rel.
intensity) 464 (100, MH+); HRESIMS m/z
C26H30N3O5: Calcd 464.2185, Found 464.2202. Anal.
Calcd for C26H29N3O5Æ0.8CHCl3: C, 57.58; H, 5.37; N,
7.52. Found: C, 57.23; H, 5.11; N, 7.34.
4.7. 11-(30-Methylaminopropylidene)-5,6-dihydro-2,3-
dimethoxy-6-methyl-8,9-methylenedioxy-5-oxo-11H-
indeno[1,2-c]isoquinoline (11)
Prepared from 2 (100mg, 0.27mmol) and 33 (61.7mg,
0.33mmol) following the procedure for 5. The chroma-
tography column was eluted with CHCl3–MeOH (5:1)