Please do not adjust margins
Page 5 of 8
New Journal of Chemistry
Journal NameARTICLE
1
2
3
4
5
6
7
8
9
1
dione (Lc). Yield = 70.0 %. 1H NMR (400 MHz, CDCl3) δ 8.48 1162, 1009, 959, 781, 747, 526, 505, 439 cm−1. H NMR (600
(d, J = 4.9 Hz, 2H), 8.39 (d, J = 7.2 Hz, 1H), 8.16 (d, J = 2.5 Hz, MHz, DMSO-d6) δ 8.76 (d, J = 5.5 Hz,D2OHI:)1,08.1.03309/(Cd9,NJJ0=10776.2A
1H), 7.99 (d, J = 8.2 Hz, 1H), 7.72-7.57 (m, 3H), 7.55-7.48 (m, Hz, 1H), 8.26 (d, J = 8.1 Hz, 3H), 7.89 (s, 1H), 7.80 (s, 2H),
4H), 7.39 (d, J = 2.4 Hz, 1H), 7.34-7.24 (m, 2H), 7.24-7.18 (m, 7.78 (d, J = 7.5 Hz, 2H), 7.63 (t, J = 6.7 Hz, 2H), 7.35 (d, J =
1H), 7.14-7.04 (m, 2H), 5.34 (s, 2H), 4.04-4.01 (m, 2H), 2.63 (t, 7.5 Hz, 2H), 7.30 (t, J = 7.5 Hz, 2H), 7.23 (t, J = 7.3 Hz, 1H),
J = 7.0 Hz, 2H), 1.93-1.80 (m, 2H), 1.78-1.70 (m, 2H). 13C 5.36 (d, J = 15.8 Hz, 2H), 5.22 (s, 2H), 4.85 (d, J = 15.9 Hz,
NMR (101 MHz, CDCl3) δ 164.3, 163.9, 157.5, 137.3, 133.2, 2H), 4.04 (s, 2H), 3.06 (s, 2H), 1.64 (s, 2H), 1.60 (s, 2H), 1.39
132.7, 129.0, 128.9, 128.5, 127.5, 127.5, 124.1, 123.7, 122.8, (s, 2H). 13C NMR (151 MHz, DMSO-d6) δ 165.81, 163.46,
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
122.5, 113.9, 100.0, 67.6, 43.6, 33.3, 32.6, 31.0, 29.3, 27.7.
163.07, 156.86, 149.01, 141.27, 137.27, 133.17, 133.09,
Data for 2-butyl-5-hydroxy-1H-benzo[de]isoquinoline- 128.35, 128.29, 127.69, 127.51, 127.07, 125.30, 123.41,
1,3(2H)-dione (I3). Yield = 95.0 %. 1H NMR (400 MHz, 123.29, 122.76, 121.98, 121.71, 114.00, 68.09, 67.82, 64.08,
DMSO-d6) δ 7.83 (dd, J = 11.7, 4.5 Hz, 2H), 7.61 (d, J = 2.4 Hz, 42.93, 40.39, 27.93, 26.70, 22.65. Elemental analysis calcd. (%)
1H), 7.32 (dd, J = 8.1, 7.4 Hz, 1H), 7.23 (d, J = 2.4 Hz, 1H), for C36H34Cl2N4O3Pt: C 51.68, H 4.10, N 6.70; found: C 51.65,
3.75-3.46 (m, 2H), 1.34-1.11 (m, 2H), 1.03-0.87 (m, 2H), 0.52 H 4.14, N 6.68.
(t, J = 7.4 Hz, 3H).
Data
Data for 3. Yield: 90.1%. ESI-MS: m/z = 786.2 [M-Cl]+.
for
5-(4-bromobutoxy)-2-butyl-1H- IR (KBr): 3408, 2925, 1698, 1584, 1440, 1329, 1272, 1163,
benzo[de]isoquinoline-1,3(2H)-dione (II4). Yield = 82.0 %. H 978, 780, 731, 705, 525, 508 cm−1. 1H NMR (600 MHz,
NMR (400 MHz, CDCl3) δ 8.43 (d, J = 7.3 Hz, 1H), 8.24 (d, J DMSO-d6) δ 8.75 (d, J = 5.6 Hz, 2H), 8.30 (d, J = 7.2 Hz, 1H),
= 2.5 Hz, 1H), 8.06 (d, J = 8.2 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 8.24 (d, J = 8.6 Hz, 3H), 7.81 (d, J = 9.1 Hz, 3H), 7.78 (d, J =
7.50 (d, J = 2.4 Hz, 1H), 4.38-4.01 (m, 4H), 3.53 (t, J = 6.3 Hz, 7.8 Hz, 2H), 7.59 (t, J = 6.6 Hz, 2H), 7.36 (d, J = 7.7 Hz, 2H),
2H), 2.20-1.99 (m, 4H), 1.75-1.67 (m, 2H), 1.49-1.40 (m, 2H), 7.31 (t, J = 7.4 Hz, 2H), 7.24 (t, J = 7.2 Hz, 1H), 5.38 (d, J =
1
0.98 (t, J = 7.3 Hz, 3H).
15.8 Hz, 2H), 5.23 (s, 2H), 4.86 (d, J = 15.8 Hz, 2H), 4.05 (s,
Data for 5-(4-(bis(pyridin-2-ylmethyl)amino)butoxy)-2- 2H), 3.14 (s, 2H), 1.74 (s, 4H). 13C NMR (151 MHz, DMSO-
butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (Ld). Yield = d6) δ 165.86, 163.51, 163.07, 156.77, 149.04, 141.31, 137.34,
67.0 %. 1H NMR (400 MHz, CDCl3) δ 8.50-8.48 (m, 2H), 8.39 133.23, 133.07, 128.43, 127.77, 127.59, 127.15, 125.34,
-8.36 (m, 1H), 8.15 (dd, J = 2.4, 1.7 Hz, 1H), 8.00 (d, J = 8.3 123.47, 123.30, 122.82, 121.95, 121.74, 114.22, 67.87, 67.77,
Hz, 1H), 7.66-7.59 (m, 3H), 7.51 (d, J = 7.7 Hz, 2H), 7.40 (s, 63.89, 43.00, 40.42, 25.33, 23.87. Elemental analysis calcd. (%)
1H), 7.14-7.04 (m, 2H), 4.13 (dd, J = 15.0, 7.4 Hz, 2H), 4.05 for C35H32Cl2N4O3Pt: C 51.10, H 3.92, N 6.81; found: C 51.05,
(dd, J = 15.2, 9.1 Hz, 2H), 2.63 (t, J = 7.0 Hz, 2H), 1.89-1.82 H 3.95, N 6.79.
(m, 2H), 1.78-1.65 (m, 4H), 1.54-1.36 (m, 2H), 0.95 (t, J = 7.3
Data for 4. Yield: 88.2%. ESI-MS: m/z = 753.1 [M-Cl]+.
Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 164.3, 163.9, 159.8, IR (KBr): 3411, 2955, 1699, 1659, 1625, 1439, 1383, 1334,
157.7, 149.0, 136.4, 133.2, 132.42, 128.4, 127.3, 124.0, 123.5, 1272, 1162, 1071, 780, 549, 440 cm−1. H NMR (600 MHz,
1
123.0, 122.7, 122.6, 122.0, 113.6, 68.4, 60.5, 53.8, 40.3, 26.8, DMSO-d6) δ 8.76 (d, J = 5.5 Hz, 2H), 8.31 (d, J = 8.0 Hz, 1H),
23.6, 20.4, 13.9.
8.26 (t, J = 7.7 Hz, 3H), 7.83 (s, 1H), 7.82 – 7.77 (m, 4H), 7.61
(t, J = 6.6 Hz, 2H), 5.34 (d, J = 15.8 Hz, 2H), 4.84 (d, J = 15.8
Hz, 2H), 4.07 (s, 2H), 4.04 (t, J = 7.4 Hz, 2H), 3.14 (s, 2H),
1.74 (s, 4H), 1.62 (s, 2H), 1.36 (d, J = 7.5 Hz, 2H), 0.93 (t, J =
7.4 Hz, 3H). 13C NMR (151 MHz, DMSO-d6) δ 165.78, 163.40,
162.98, 156.74, 149.02, 141.28, 133.02, 132.92, 128.11,
127.70, 125.32, 123.51, 123.40, 122.78, 121.93, 121.71,
113.90, 67.84, 67.68, 63.80, 40.39, 29.62, 25.29, 23.80, 19.77,
13.70. Elemental analysis calcd. (%) for C32H34Cl2N4O3Pt: C
48.74, H 4.35, N 7.10; found: C 48.70, H 4.37, N 7.08.
Synthesis of 1−4
Four Pt(II) complexes 1−4 were obtained by the reaction of
La−Ld ligands with cis-Pt(DMSO)2Cl2 at a 1.0:1.0 ratio in 30.0
mL CH3CN at 80 C for 6.0 h (Scheme 1).
Data for 1. Yield: 85.3%. ESI-MS: m/z = 773.0 [M-Cl]+.
IR (KBr): 3403, 2934, 1703, 1662, 1626, 1487, 1438, 1377,
1338, 1279, 1248, 1222, 1165, 1185, 1106, 880, 781, 767, 697,
1
546, 440 cm−1. H NMR (600 MHz, DMSO-d6) δ 8.75 (d, J =
5.5 Hz, 2H), 8.30 (t, J = 8.3 Hz, 2H), 8.25 (t, J = 8.2 Hz, 2H),
7.84 (s, 1H), 7.82 (s, 2H), 7.80 (d, J = 9.0 Hz, 2H), 7.61 (t, J =
Methods and evaluation
6.6 Hz, 2H), 7.54 (t, J = 7.5 Hz, 2H), 7.47 (s, 1H), 7.39 (d, J = The in vitro and in vivo anti-tumor activities of 3 and 4 were
7.2 Hz, 2H), 5.40 (d, J = 15.8 Hz, 2H), 4.88 (d, J = 15.8 Hz, evaluated and analyzed according to Metzler-Nolte, Liang,
2H), 4.08 (s, 2H), 3.15 (s, 2H), 1.75 (s, 4H). 13C NMR (151 Chao and Lippard et al. reported44,45,51,69,76−80. In addition, the
MHz, DMSO-d6) δ 165.83, 163.67, 163.22, 156.69, 148.98, detailed experimental methods were described in the Electro
141.27, 135.96, 133.15, 133.09, 129.06, 128.88, 128.22, Supporting Information Materials.
128.09, 127.67, 125.31, 123.96, 123.43, 123.20, 122.39,
121.74, 113.96, 67.80, 67.74, 63.82, 40.39, 25.29, 23.80.
Elemental analysis calcd. (%) for C34H30Cl2N4O3Pt: C 50.50, H
Acknowledgements
3.74, N 6.93; found: C 50.45, H 3.76, N 6.90.
We thank the National Natural Science Foundation of China
(Nos. 21867017, 21861014 and 21761033), the Natural Science
Foundation of Guangxi (Nos. 2018GXNSFBA138021,
Data for 2. Yield: 80.6%. ESI-MS: m/z = 801.1 [M-Cl]+.
IR (KBr): 3400, 2937, 1698, 1659, 1624, 1439, 1331, 1271,
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2019, 00, 1-7 | 5
Please do not adjust margins