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2H), 3.05 (s, 2H), 2.67 (s, 2H), 2.57 (t, J = 7.2 Hz, 2H), 1.94–1.83 (m,
4H), 1.62 (dd, J = 14.4, 7.3 Hz, 2H), 1.53–1.42 (m, 2H), 1.35–1.22 (m,
8H). 13C NMR (100 MHz, CDCl3) d 158.21, 150.83, 148.76, 147.26,
143.47, 135.07, 134.01, 128.46, 128.24, 123.50, 122.86, 120.11,
115.66, 107.43, 102.18, 101.23, 56.53, 53.98, 49.40, 49.21, 33.86,
31.69, 29.92, 29.37, 29.24, 27.19, 26.82, 24.72, 23.00, 22.71. Purity:
97.5% by HPLC, HRMS (ESI): calcd for (MÀH)À (C30H39N3O3)
requires m/z 488.2913, found 488.2918.
1.36–1.24 (m, 8H). 13C NMR (100 MHz, CDCl3) d 158.21, 153.14,
150.82, 147.27, 136.81, 136.17, 128.47, 128.24, 123.50, 122.86,
120.11, 115.67, 104.95, 60.76, 56.04, 54.31, 49.49, 49.40, 33.87,
31.68, 29.96, 29.39, 29.25, 27.22, 26.83, 24.72, 23.00, 22.71. Purity:
98.5% by HPLC, HRMS (ESI): calcd for (MÀH)À (C31H43N3O3)
requires m/z 504.3226, found 504.3226.
4.4.10. N1-(1,2,3,4-Tetrahydroacridin-9-yl)-N9-(3,4,5-trimethoxy-
benzyl)nonane-1,9-diamine (9j)
4.4.6. N1-((7-Methoxybenzo[d][1,3]dioxol-5-yl)methyl)-N9-(1,2,
3,4-tetrahydroacridin-9-yl)nonane-1,9-diamine (9f)
Aldehyde 4b was treated with 8f according to general proce-
dure to give the desired product 9j as light yellow oil (74% yield).
1H NMR (400 MHz, CDCl3) d 7.95 (d, J = 8.1 Hz, 1H), 7.90 (d,
J = 8.0 Hz, 1H), 7.52 (t, J = 7.1 Hz, 1H), 7.32 (s, 1H), 6.57 (s, 2H),
3.85 (s, 6H), 3.83 (s, 3H), 3.72 (s, 2H), 3.46 (t, J = 7.2 Hz, 2H), 3.05
(s, 2H), 2.68 (s, 2H), 2.65–2.59 (m, 2H), 1.90 (dd, J = 6.2, 3.1 Hz,
4H), 1.69–1.58 (m, 2H), 1.54–1.47 (m, 2H), 1.38–1.27 (m, 10H).
13C NMR (100 MHz, CDCl3) d 158.22, 153.15, 150.84, 147.26,
136.84, 135.95, 128.44, 128.23, 123.48, 122.86, 120.10, 115.63,
105.01, 60.76, 56.04, 54.20, 49.40, 33.82, 31.69, 29.87, 29.40,
29.38, 29.24, 27.27, 26.85, 24.71, 22.99, 22.70. Purity: 99.4% by
HPLC, HRMS (ESI): calcd for (MÀH)À (C32H45N3O3) requires m/z
518.3383, found 518.3389.
Intermediate 4a was treated with 8f according to general proce-
dure to give the desired product 9f as light yellow oil (63% yield).
1H NMR (400 MHz, CDCl3) d 7.95 (d, J = 8.4, 1H), 7.90 (d, J = 8.4,
1H), 7.53 (t, J = 7.3, 1H), 7.33 (d, J = 7.4, 1H), 6.50 (s, 2H), 5.92 (s,
2H), 3.88 (s, 3H), 3.67 (s, 2H), 3.47 (t, J = 7.2, 2H), 3.05 (s, 2H),
2.68 (s, 2H), 2.58 (t, J = 7.3, 2H), 1.94–1.83 (m, 4H), 1.69–1.59 (m,
2H), 1.48 (dd, J = 13.8, 7.0, 2H), 1.37–1.24 (m, 10H). 13C NMR
(100 MHz, CDCl3)
d 158.26, 150.85, 148.78, 147.29, 143.50,
134.87, 134.07, 128.49, 128.26, 123.51, 122.86, 120.12, 115.67,
107.48, 102.24, 101.27, 56.54, 53.92, 49.45, 49.16, 33.85, 31.72,
29.87, 29.41, 29.38, 29.26, 27.26, 26.87, 24.74, 23.02, 22.72. Purity:
98.9% by HPLC, HRMS (ESI): calcd for (MÀH)À (C31H41N3O3)
requires m/z 502.3070, found 502.3077.
4.4.11. N1-(3,4-Dimethoxybenzyl)-N6-(1,2,3,4-tetrahydroacridin-
9-yl)hexane-1,6-diamine (9k)
4.4.7. N1-(1,2,3,4-Tetrahydroacridin-9-yl)-N6-(3,4,5-trimethoxy-
benzyl)hexane-1,6-diamine (9g)
Aldehyde 4c was treated with 8c according to general proce-
dure to give the desired product 9k as light yellow oil (88% yield).
1H NMR (400 MHz, CDCl3) d 7.92 (dd, J = 12.5, 8.6 Hz, 2H), 7.51 (t,
J = 7.6 Hz, 1H), 7.30 (d, J = 7.6 Hz, 1H), 6.87 (s, 1H), 6.80 (q,
J = 8.3 Hz, 2H), 3.96 (s, 1H), 3.84 (d, J = 11.2 Hz, 6H), 3.69 (s, 2H),
3.44 (t, J = 6.9 Hz, 2H), 3.04 (s, 2H), 2.66 (s, 2H), 2.58 (t, J = 7.1 Hz,
2H), 2.51 (s, 1H), 1.88 (s, 4H), 1.61 (dd, J = 13.9, 7.0 Hz, 2H),
1.55–1.44 (m, 2H), 1.42–1.29 (m, 4H). 13C NMR (100 MHz, CDCl3)
d 158.33, 150.70, 148.91, 147.96, 147.39, 132.97, 128.59, 128.17,
123.49, 122.81, 120.19, 115.80, 111.44, 111.04, 55.87, 55.81,
53.80, 49.34, 49.21, 33.94, 31.65, 29.88, 27.07, 26.81, 24.74,
23.01, 22.73. Purity: 98.9% by HPLC, HRMS (ESI): calcd for
(MÀH)À (C28H37N3O2) requires m/z 446.2808, found 446.2811.
Aldehyde 4b was treated with 8c according to general proce-
dure to give the desired product 9g as light yellow oil (75% yield).
1H NMR (400 MHz, CDCl3) d 7.92 (dd, J = 16.0, 7.8 Hz, 2H), 7.52 (t,
J = 7.0 Hz, 1H), 7.31 (t, J = 7.0 Hz, 1H), 6.55 (s, 2H), 3.83 (d,
J = 4.3 Hz, 9H), 3.70 (s, 2H), 3.45 (t, J = 7.2 Hz, 2H), 3.04 (d,
J = 6.1 Hz, 2H), 2.67 (t, J = 5.3 Hz, 2H), 2.61 (t, J = 7.2 Hz, 2H), 2.30
(s, 1H), 1.93–1.84 (m, 4H), 1.69–1.58 (m, 2H), 1.57–1.45 (m, 2H),
1.42–1.32 (m, 4H). 13C NMR (100 MHz, CDCl3) d 158.35, 153.14,
150.69, 147.42, 136.78, 136.21, 128.64, 128.17, 123.50, 122.81,
120.20, 115.83, 104.90, 60.80, 56.07, 54.35, 49.36, 34.00, 31.68,
29.95, 27.10, 26.84, 24.75, 23.02, 22.75. Purity: 99.4% by HPLC,
HRMS (ESI): calcd for (MÀH)À (C29H39N3O3) requires m/z
476.2913, found 476.2919.
4.4.12. N1-(3,4-Dimethoxybenzyl)-N7-(1,2,3,4-tetrahydroacridin-
9-yl)heptane-1,7-diamine (9l)
4.4.8. N1-(1,2,3,4-Tetrahydroacridin-9-yl)-N7-(3,4,5-trimethoxy-
benzyl)heptane-1,7-diamine (9h)
Aldehyde 4c was treated with 8d according to general proce-
dure to give the desired product 9l as light yellow oil (65% yield).
1H NMR (400 MHz, CDCl3) d 7.93 (dd, J = 14.0, 8.5 Hz, 2H), 7.52 (t,
J = 7.6 Hz, 1H), 7.34–7.30 (m, 1H), 6.91 (s, 1H), 6.84 (d, J = 8.2 Hz,
1H), 6.79 (d, J = 8.1 Hz, 1H), 3.87 (s, 3H), 3.83 (s, 3H), 3.73 (s, 2H),
3.46 (t, J = 7.2 Hz, 2H), 3.05 (s, 2H), 2.67 (s, 2H), 2.61 (t, J = 7.3 Hz,
2H), 1.99 (s, 1H), 1.94–1.82 (m, 4H), 1.69–1.58 (m, 2H),
1.56–1.45 (m, 2H), 1.41–1.25 (m, 6H). 13C NMR (100 MHz, CDCl3)
d 158.11, 150.92, 148.97, 148.18, 147.06, 131.80, 128.34, 128.27,
123.55, 122.85, 120.52, 120.03, 115.59, 111.67, 111.06, 55.87,
55.83, 53.28, 49.34, 48.79, 33.66, 31.62, 29.32, 29.16, 27.13,
26.79, 24.71, 22.96, 22.65. Purity: 99.9% by HPLC, HRMS (ESI): calcd
for (MÀH)À (C29H39N3O2) requires m/z 460.2964, found 460.2971.
Aldehyde 4b was treated with 8d according to general proce-
dure to give the desired product 9h as light yellow oil (66% yield).
1H NMR (400 MHz, CDCl3) d 7.97 (d, J = 8.5 Hz, 1H), 7.92 (d,
J = 8.5 Hz, 1H), 7.53 (t, J = 7.6 Hz, 1H), 7.32 (t, J = 7.7 Hz, 1H), 6.61
(s, 2H), 5.06 (s, 1H), 3.84 (s, 6H), 3.82 (s, 3H), 3.77 (s, 2H), 3.50 (t,
J = 7.2 Hz, 2H), 3.04 (s, 2H), 2.65 (t, J = 7.3 Hz, 4H), 1.99 (s, 1H),
1.87 (s, 4H), 1.73–1.59 (m, 2H), 1.55 (s, 2H), 1.34 (d, J = 15.9 Hz,
6H). 13C NMR (100 MHz, CDCl3) d 157.13, 153.17, 151.53, 145.85,
137.17, 133.77, 128.78, 127.08, 123.67, 123.03, 119.42, 114.86,
105.53, 60.72, 56.05, 53.28, 49.09, 48.45, 32.78, 31.47, 29.04,
28.77, 27.00, 26.69, 24.57, 22.78, 22.33. Purity: 99.7% by HPLC,
HRMS (ESI): calcd for (MÀH)À (C30H41N3O3) requires m/z
490.3070, found 490.3074.
4.4.13. N1-(3,4-Dimethoxybenzyl)-N8-(1,2,3,4-tetrahydroacridin-
9-yl)octane-1,8-diamine (9m)
4.4.9. N1-(1,2,3,4-Tetrahydroacridin-9-yl)-N8-(3,4,5-trimethoxy-
benzyl)octane-1,8-diamine (9i)
Aldehyde 4c was treated with 8e according to general proce-
dure to give the desired product 9m as light yellow oil (69% yield).
1H NMR (400 MHz, CDCl3) d 7.94 (d, J = 8.4 Hz, 1H), 7.90 (d,
J = 8.4 Hz, 1H), 7.52 (t, J = 7.3 Hz, 1H), 7.31 (t, J = 7.5 Hz, 1H), 6.88
(d, J = 1.2 Hz, 1H), 6.84–6.76 (m, 2H), 3.87 (s, 3H), 3.83 (s, 3H),
3.71 (s, 2H), 3.45 (t, J = 7.2 Hz, 2H), 3.04 (d, J = 5.7 Hz, 2H), 2.67
(s, 2H), 2.60 (t, J = 7.2 Hz, 2H), 1.95–1.84 (m, 4H), 1.68–1.57 (m,
2H), 1.55–1.44 (m, 2H), 1.36–1.24 (m, 8H). 13C NMR (100 MHz,
CDCl3) d 158.27, 150.79, 148.93, 147.97, 147.34, 132.95, 128.54,
Aldehyde 4b was treated with 8e according to general proce-
dure to give the desired product 9i as light yellow oil (83% yield).
1H NMR (400 MHz, CDCl3) d 7.95 (d, J = 8.5 Hz, 1H), 7.91 (d,
J = 8.4 Hz, 1H), 7.52 (t, J = 7.6 Hz, 1H), 7.32 (t, J = 7.6 Hz, 1H), 6.56
(s, 2H), 3.85 (s, 6H), 3.83 (s, 3H), 3.71 (s, 2H), 3.45 (d, J = 7.2 Hz,
2H), 3.05 (s, 2H), 2.68 (s, 2H), 2.62 (t, J = 7.2 Hz, 2H), 1.94–1.84
(m, 4H), 1.69–1.58 (m, 2H), 1.49 (dd, J = 13.1, 6.4 Hz, 2H),