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5479
5.8.10.4. 4-(4-Methylpiperazine-1-carbonyl)-9-(2-(1H-
indol-3-yl)-ethylamino)-(10H)-acridine (19d). Yield:
71.2%; H NMR (600 MHz, CDCl3) d 2.18 (br s, 1H),
2.32 (s, 3H), 2.43 (br s, 1H), 2.58 (br s, 1H), 2.69 (br
s, 1H), 3.25 (br s, 4H), 3.88 (br s, 1H), 4.2 (br s, 3H),
5.28 (br s, 1H), 7.07 (br s, 1H), 7.15 (t, 1H), 7.25 (m,
3H), 7.42 (d, 1H), 7.61 (m, 2H), 7.64 (d, 1H), 7.97 (br
m, 3H), 8.14 (br s, 1H); HRMS (C29H30N5O) [M+H]+:
found m/z 464.2414, calcd 464.2445.
1H), 7.63 (d, 1H), 7.84 (br s, 1H), 7.94 (d, 1H), 8.06
(d, 1H), 8.10 (s, 1H), 8.48 (br s, 1H); HRMS
(C28H29N4O) [M+H]+: found m/z 437.2308, calcd
437.2336.
1
5.8.10.11.
2-(4-Methylpiperazine-1-carbonyl)-9-(1-
benzylpiperidin-4-ylamino)-(10H)-acridine (19k). Yield:
73.6%; 1H NMR (600 MHz, CDCl3) d 1.75 (br m,
2H), 2.08 (br m, 4H), 2.35 (s, 3H), 2.48 (br s, 4H),
2.88 (br s, 2H), 3.52 (s, 2H), 3.61 (br s, 2H), 3.88 (br
m, 3H), 4.84 (br s, 1H), 7.26 (m, 1H), 7.31 (m, 4H),
7.45 (t, 1H), 7.69 (d, 1H), 7.73 (t, 1H), 8.07 (d, 1H),
8.13 (m, 3H); HRMS (C31H36N5O) [M+H]+: found m/
z 494.2882, calcd 494.2914.
5.8.10.5. 4-(Morpholine-4-carbonyl)-9-(2-(1H-indol-3-
yl)-ethylamino)-(10H)-acridine (19e). Yield: 72.0%; 1H
NMR (600 MHz, CDCl3) d 3.23 (br s, 4H), 3.46 (br s,
1H), 3.87 (br m, 4H), 4.19 (br s, 3H), 5.29 (br s, 1H),
7.06 (br s, 1H), 7.16 (t, 1H), 7.25 (m, 3H), 7.41 (d,
1H), 7.62 (m, 2H), 7.65 (d, 1H), 7.95 (br m, 3H), 8.18
(br s, 1H); HRMS (C28H27N4O2) [M+H]+: found m/z
451.2106, calcd 451.2128.
5.8.10.12. N,N-Diethyl-9-(1-benzylpiperidin-4-ylami-
no)-(10H)-acridine-2-carboxamide (19l). Yield: 50.7%;
1H NMR (600 MHz, CDCl3) d 1.23 (br s, 6H), 1.75
(br m, 2H), 2.07 (br m, 4H), 2.87 (br m, 2H), 3.41 (br
s, 2H), 3.51 (s, 2H), 3.63 (br s, 2H), 3.88 (br s, 1H),
4.76 (br s, 1H), 7.26 (m, 1H), 7.30 (m, 4H), 7.44 (t,
1H), 7.68 (d, 1H), 7.74 (t, 1H), 8.07 (d, 1H), 8.12 (m,
2H), 8.22 (s, 1H); HRMS (C30H35N4O) [M+H]+: found
m/z 467.2776, calcd 467.2805.
5.8.10.6. N,N-Diethyl-9-(2-(1H-indol-3-yl)-ethylami-
no)-(10H)-acridine-4-carboxamide (19f). Yield: 52.6%;
1H NMR (600 MHz, CDCl3) d 1.02 (br s, 3H), 1.41
(br s, 3H), 3.22 (br s, 2H), 3.75 (br m, 2H), 4.18 (br s,
2H), 5.22 (br s, 2H), 7.03 (br s, 1H), 7.14 (t, 1H), 7.25
(m, 3H), 7.40 (d, 1H), 7.56 (m, 2H), 7.65 (d, 1H), 7.96
(br m, 3H), 8.23 (br s, 1H); HRMS (C28H29N4O)
[M+H]+: found m/z 437.2320, calcd 437.2336.
5.8.10.13.
2-(4-Methylpiperazine-1-carbonyl)-9-(2-
(1H-indol-3-yl)-ethylamino)-(10H)-acridine (19m). Yield:
60.3%; 1H NMR (600 MHz, CDCl3) d 2.32 (s, 3H), 2.42
(br s, 4H), 3.23 (t, 2H), 3.49 (br s, 2H), 3.82 (br s, 2H),
4.23 (t, 2H), 7.14 (m, 2H), 7.24 (t, 1H), 7.30 (t, 1H), 7.42
(d, 1H), 7.64 (m, 3H), 7.94 (d, 1H), 8.04 (t, 2H), 8.07 (s,
1H), 8.43 (br s, 1H); HRMS (C29H30N5O) [M+H]+:
found m/z 464.2415, calcd 464.2445.
5.8.10.7. 3-(4-Methylpiperazine-1-carbonyl)-9-(1-ben-
zylpiperidin-4-ylamino)-(10H)-acridine (19g). Yield:
1
40.1%; H NMR (600 MHz, CDCl3) d 1.76 (br m, 2H),
2.08 (br m, 4H), 2.34 (s, 3H), 2.41 (br s, 2H), 2.54 (br s,
2H), 2.88 (br s, 2H), 3.52 (s, 2H), 3.61 (br s, 2H), 3.88
(br s, 3H), 4.74 (br s, 1H), 7.26 (m, 1H), 7.31 (m, 4H),
7.46 (m, 2H), 7.73 (t, 1H), 8.07 (d, 1H), 8.08 (s, 1H),
8.12 (d, 1H), 8.14 (d, 1H); HRMS (C31H36N5O)
[M+H]+: found m/z 494.2894, calcd 494.2914.
5.8.10.14. N,N-Diethyl-9-(2-(1H-indol-3-yl)-ethylami-
no)-(10H)-acridine-2-carboxamide (19n). Yield: 82.8%;
1H NMR (600 MHz, CDCl3) d 1.11 (br s, 3H), 1.28
(br s, 3H), 3.22 (t, 2H), 3.26 (br s, 2H), 3.58 (br s,
2H), 4.24 (t, 2H), 7.11 (s, 1H), 7.15 (t, 1H), 7.24 (t,
1H), 7.30 (t, 1H), 7.42 (d, 1H), 7.64 (m, 3H), 7.93 (d,
1H), 7.97 (s, 1H), 8.01 (br s, 2H), 8.43 (br s, 1H); HRMS
(C28H29N4O) [M+H]+: found m/z 437.2310, calcd
437.2336.
5.8.10.8.
N,N-Diethyl-9-(1-benzylpiperidin-4-ylami-
no)-(10H)-acridine-3-carboxamide (19h). Yield: 10.4%;
1H NMR (600 MHz, CDCl3) d 1.17 (br s, 3H), 1.30
(br s, 3H), 1.75 (br m, 2H), 2.07 (br m, 4H), 2.88 (br
m, 2H), 3.41 (br s, 2H), 3.52 (s, 2H), 3.63 (br s, 2H),
3.87 (br s, 1H), 4.72 (br s, 1H), 7.26 (m, 1H), 7.31 (m,
4H), 7.43 (m, 2H), 7.72 (t, 1H), 8.07 (m, 2H), 8.12 (m,
2H); HRMS (C30H35N4O) [M+H]+: found m/z
467.2779, calcd 467.2805.
5.8.10.15. N,N-Diethyl-9-amino-(10H)-acridine-2-car-
boxamide (19o). Yield: 72.4%; 1H NMR (300 MHz,
CDCl3) d 1.24 (br s, 6H), 3.38 (br s, 2H), 3.59 (br s,
2H), 5.70 (br s, 2H), 7.43 (t, 1H), 7.66 (d, 1H), 7.73 (t,
1H), 7.91 (d, 1H), 8.08 (m, 3H); HRMS (C18H20N3O)
[M+H]+: found m/z 294.1588, calcd 294.1601.
5.8.10.9. 3-(4-Methylpiperazine-1-carbonyl)-9-(2-(1H-
indol-3-yl)-ethylamino)-(10H)-acridine
(19i).
Yield:
29.6%; 1H NMR (600 MHz, CDCl3) d 2.33 (s, 3H),
2.39 (br s, 2H), 2.52 (br s, 2H), 3.25 (t, 2H), 3.56 (br s,
2H), 3.87 (br s, 2H), 4.23 (t, 2H), 7.09 (s, 1H), 7.17 (t,
1H), 7.26 (t, 1H), 7.31 (m, 2H), 7.43 (d, 1H), 7.67 (m,
2H), 7.92 (d, 1H), 7.96 (d, 1H), 8.02 (s, 1H), 8.06 (d,
1H), 8.21 (br s, 1H); HRMS (C29H30N5O) [M+H]+:
found m/z 464.2414, calcd 464.2445.
5.8.10.16. N,N-Diethyl-9-(2-(dimethylamino)ethylami-
no)-(10H)-acridine-2-carboxamide (19p). Yield: 51.2%;
1H NMR (300 MHz, CDCl3) d 1.24 (br s, 6H), 2.37 (s,
3H), 2.62 (t, 2H), 3.49 (br s, 4H), 3.91 (t, 2H), 7.38 (t,
1H), 7.64 (d, 1H), 7.69 (t, 1H), 8.064 (d, 1H), 8.07 (d,
1H), 8.17 (d, 1H), 8.27 (s, 1H); HRMS (C22H29N4O)
[M+H]+: found m/z 365.2307, calcd 365.2336.
5.8.10.10. N,N-Diethyl-9-(2-(1H-indol-3-yl)-ethylami-
no)-(10H)-acridine-3-carboxamide (19j). Yield: 45.5%;
1H NMR (600 MHz, CDCl3) d 1.14 (br s, 3H), 1.30
(br s, 3H), 3.32 (br s, 4H), 3.60 (br s, 2H), 4.29 (br s,
2H), 7.13 (m, 2H), 7.24 (m, 3H), 7.43 (d, 1H), 7.59 (t,
5.8.10.17.
N,N-Diethyl-9-(4-methylpiperazin-1-yl)-
(10H)-acridine-2-carboxamide (19q). Yield: 43.1%; 1H
NMR (300 MHz, DMSO-d6) d 1.18 (br s, 6H), 2.33 (s,
3H), 2.64 (t, 4H), 3.36 (br s, 4H), 3.61 (t, 4H), 7.56 (t,