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V. S. Gopinath et al. / Bioorg. Med. Chem. 16 (2008) 474–487
126.87(C3), 120.12(C4), 118.73(C5), 136.74(C6), 122.12(C7),
4.3.2.10.
10-(40-N-Diethylaminobutyl)-2-chloroacri-
0
134.97(C8), 175.34(C9), 127.88(C9 ), 140.24(C4 ), 141.18(C10 ),
0
0
done (11). The procedure used for 3 was followed with
1.2 g (3.8 mmol) of 10, 1.57 g of KI, 2.64 g of K2CO3,
and 1.3 g (17.8 mmol) of N,N-diethylamine. The prod-
uct was purified by column chromatography to give a
yellow oily product which was converted into its hydro-
chloride form of 11 (yield 0.73 g, 50%, mp 100–104 ꢁC).
UV kmax (e) (MeOH): 216 (23,266), 255 (36,367), 392
(6864) nm. IR: 3386, 2941, 1625, 1458, 1276, 960,
0
121.46(C8 ), 57.53(Ck), 23.46(Cl), 51.26(Cm), 53.33(Ca
and Cb) and 22.90(Cc and Cd). MS: m/z (%) 342
[(M+H)+, 100].
4.3.2.7. 10-(30-N-Morpholinopropyl)-2-chloroacridone
(8). Compound 8 as its hydrochloride salt (yield 0.6 g,
43%, mp 248–250 ꢁC) was obtained by following the
procedure of 3 with 1.1 g of 2 (3.59 mmol), 1.55 g KI,
2.5 g of K2CO3, and 1.17 g (13.4 mmol) of morpholine.
UV kmax (e) (MeOH): 217 (23,445), 256 (54,741), 389
(7075), 408 (11,260) nm. IR: 3429, 2869, 1617, 1494,
1
756 cmꢁ1. H NMR (DMSO-d6): d 7.35–8.35 (m, Ar-
H, 7H, H1, H3, H4 and H5–H8), 4.48–4.52 (t, 2H, Hk),
3.08–3.81 (m, 8H, Hm, Ha, Hb), 1.22–1.26 (m, 6H, Hc
and Hd) and 1.83–2.5 (t, 4H, Hl, Hn). 13C NMR
(DMSO-d6): d 126.80(C1), 122.57(C2), 125.41(C3),
118.76(C4), 116.16(C5), 134.60(C6), 121.78(C7), 133.83(C8),
1272, 874, 684 cmꢁ1
.
1H NMR (DMSO-d6): d 7.36–
8.35 (m, Ar-H, 7H, H1, H3, H4 and H5–H8), 3.04–3.10
(t, 4H, Hc and Hd), 2.27 (m, 4H, Hk, Hm), 2.50 (t, 4H,
Ha, Hb), and 1.21–1.97 (m, 2H, Hl). 13C NMR
0
0
0
175.46(C9), 125.93(C9 ), 140.13(C4 ), 141.37(C10 ),
0
121.55(C8 ),
54.76(Ck),
17.56(Cl),
24.20(Cm),
(DMSO-d6):
118.15(C4), 115.64(C5), 135.32(C6), 121.99(C7), 134.47(C8),
d
126.77(C1), 122.34(C2), 125.33(C3),
45.15(Cn), 50.41(Ca and Cb) and 8.50(Cc and Cd). MS:
m/z (%) 358 [(M+H)+, 100]. Anal. (C21H26N2OCl2) C,
H, N.
0
176.34(C9), 126.52(C9 ), 139.72(C4 ), 141.00(C10 ),
0
0
0
121.08(C8 ), 53.08(Ck), 21.12(Cl), 42.57(Cm), 51.39(Ca
and Cb) and 63.27(Cc and Cd). MS: m/z (%) 358
4.3.2.11. 10-(40-N-(Methylpiperazino)butyl)-2-chloro-
acridone (12). Amounts of 1.1 g of 10 (3.43 mmol),
1.42 g of KI, 2.37 g of K2CO3, and 1.56 g (15.6 mmol)
of N-methylpiperazine were refluxed and processed
according to the procedure used for 11. The crude prod-
uct was chromatographed on silica gel to get the pure
base which was then converted into hydrochloride salt
of 10-(40-N-(methylpiperazino)butyl)-2-chloroacridone
12 (yield 0.8 g, 57%, mp 260–262 ꢁC). UV kmax (e)
(MeOH): 216 (18,164), 256 (59,249), 392 (16,542), 412
(18,380) nm. IR: 3445, 2829, 1716, 1634, 1480, 1253,
[(M+H)+, 100]. Anal. (C20H22N2O2Cl2) C, H, N.
4.3.2.8. 10-(30-N-[Bis[hydroxyethyl]amino]propyl)-2-
chloroacridone (9). The experimental steps used for 3
were repeated with 1 g (3.26 mmol) of 2, 1.48 g of
KI, 2.3 g of K2CO3, and 0.88 g (8.34 mmol) of N,N-
diethanolamine. The crude product was purified by col-
umn chromatography to give a light yellow solid 9
(yield 0.65 g, 48%, mp 148–150 ꢁC). UV kmax (e)
(MeOH): 216 (30,000), 255 (61,447), 386 (9659), 402
(10,681) nm. IR: 3286, 2973, 2885, 1630, 1488, 1267,
1
962, 754, 652 cmꢁ1. H NMR (DMSO-d6): d 7.34–8.32
960, 757, 682 cmꢁ1
.
1H NMR (DMSO-d6): d 7.35–
(m, Ar-H, 7H, H1, H3, H4 and H5–H8), 2.8–3.7 (m,
12H, Hk, Hm, Ha, Hb, Hc, Hd), 2.5 (s, 3H, He) and
1.84–2.5 (m, 4H, Hl, Hm). 13C NMR (DMSO-d6): d
126.77(C1), 122.51(C2), 125.37(C3), 118.73(C4), 116.12(C5),
8.34 (m, Ar-H, 7H, H1 H3, H4 and H5–H8),
3.25–3.28 (t, 4H, Hk, Hm), 3.53–3.79 (t, 8H, Ha, Hb),
3.81–3.92 (m, 4H, Hc and Hd), 2.5 (s, 2H, He and
Hf, disappearing on D2O exchange), and 2.07–2.08
(q, 2H, Hl). 13C NMR (DMSO-d6): d 128.38(C1),
122.55(C2), 126.65(C3), 116.04(C4), 113.83(C5), 136.50(C6),
134.61(C6),
121.76(C7),
133.84(C8),
175.44(C9),
0
0
0
0
125.90(C9 ), 140.06(C4 ), 141.31(C10 ), 121.51(C8 ),
55.20(Ck), 20.23(Cl), 20.06(Cm), 45.16(Cn), 49.43(Ca
and Cb), 48.05(Cc and Cd) and 42.02(Ce). MS: m/z (%)
385 [(M+H)+, 100].
0
0
121.23(C7), 134.69(C8), 175.36(C9), 121.88(C9 ), 140.32(C4 ),
0
141.22(C10 ),
0
118.80(C8 ),
47.36(Ck),
21.09(Cl),
42.78(Cm), 46.22(Ca and Cb) and 8.52(Cc and Cd). MS:
m/z (%) 376 [(M+H)+, 100]. Anal. (C20H23N2O3Cl) C,
H, N.
4.3.2.12. 10-(40-N-Piperidinobutyl)-2-chloroacridone
(13). Compound 10 (1.5 g, 4.68 mmol), KI (1.94 g),
K2CO3 (3.23 g), and piperidine (1.4 g, 23.42 mmol) were
used for this reaction and the rest of the steps used for
12 remains the same. The oily residue was then con-
verted into hydrochloride salt of 13 (yield 1 g, 70%,
mp 199–200 ꢁC). UV kmax (e) (MeOH): 217 (15,900),
259 (36,500), 393 (8367), 411 (9400) nm. IR: 3400,
4.3.2.9. 10-(40-Chlorobutyl)-2-chloroacridone (10).
Yellow crystals of compound 10 in the pure form (yield
6.5 g, 55%, mp 101–106 ꢁC) were prepared by following
the procedure used for 2 with 6 g (0.026 mol) of 2-chlo-
roacridone and 1-bromo-4-chlorobutane (0.065 mmol).
UV kmax (e) (MeOH): 217 (15,914), 254 (31,930), 392
(8004), 412 (8687) nm. IR: 3395, 2928, 1614, 1591,
1
2880, 1629, 1595, 1459, 1263, 959, 758, 682 cmꢁ1. H
NMR (DMSO-d6): d 7.36–8.36 (m, Ar-H, 7H, H1, H3,
H4 and H5–H8), 3.31–3.41 (m, 8H, Hk, Hm), 1.38–1.40
(m, 8H, Ha, Hb, Hc and Hd). 1.68–1.96 (m, 2H, He)
and 2.81–2.84 (q, 4H, Hn, Hl). 13C NMR (DMSO-d6):
1
1256, 965, 752 cmꢁ1. H NMR (DMSO-d6): d 7.25–8.3
(m, Ar-H, 7H, H1, H3, H4 and H5–H8), 3.61–3.73 (t,
4H, Hk, Hm), and 1.86–3.34 (m, 4H, Hl, Hm). 13C
NMR
125.40(C3), 118.47(C4), 115.95(C5), 134.48(C6), 121.64(C7),
(DMSO-d6):
d
126.75(C1),
122.51(C2),
d 126.84(C1), 122.57(C2), 125.44(C3), 118.72(C4),
116.12(C5), 134.62(C6), 121.80(C7), 133.86(C8), 175.41(C9),
0
0
133.75(C8), 175.37(C9), 125.86(C9 ), 140.03(C4 ),
0
0
0
0
125.95(C9 ), 140.14(C4 ), 141.37(C10 ), 121.58(C8 ),
55.44(Ck), 20.35(Cl), 24.32(Cm), 45.04(Cn), 49.43(Ca
and Cb) and 48.05(Cc and Cd). MS: m/z (%) 370
[(M+H)+, 100]. Anal. (C22H26N2OCl2) C, H, N.
0
0
141.29(C10 ),
117.67(C8 ),
44.70(Ck),
25.51(Cl),
29.26(Cm) and 44.96(Cn). MS: m/z (%) 320 [(M+H)+,
100]. Anal. (C17H15NOCl2) C, H, N.