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. Author manuscript; available in PMC: 2012 Apr 28.
Published in final edited form as: J Med Chem. 2011 Apr 6;54(8):2668–2679. doi: 10.1021/jm101417n

Table 1.

Analogues and derivatives of oncrasin-1 and their antitumor activities (IC50, μM)

graphic file with name nihms285028u1.jpg
Compounds R1 R2 R3 Indole Ring T29 Cells μM T29Kt1Cells μM H460 Cells μM
Oncrasin−1 CHO 4′-Cl Ph H >31.6 2.51 0.25
1 CHO 2′-F Ph H >31.6 0.31 0.1
2 CHO 3′-F Ph H >31.6 2.63 0.031
3 CHO 3′-Cl Ph H >31.6 0.37 0.037
4 CHO 3′-Br Ph H >31.6 1.58 0.039
5 CHO 4′-Br Ph H >31.6 0.25 0.031
6 CHO 3′-CF3Ph H >31.6 1.78 0.14
7 CHO 4′-CF3Ph H >31.6 >31.6 1.58
8 CHO 3′-MePh H >31.6 6.3 0.039
9 CHO 4′-MePh H >31.6 3.98 0.063
10 CHO 3′-NO2Ph H >31.6 0.50 0.039
11 CHO 4′-NO2 Ph H >31.6 10.0 0.50
12 CHO 2′,4′-2Cl Ph H >31.6 1.58 0.1
13 CHO 3′,4′-2Br Ph H >31.6 0.63 0.063
14 CHO Ph H >31.6 5.0 0.045
15 CHO 4′-Cl (CH2)2OPh H >31.6 4.89 0.045
16 CHO 3′-Cl Ph 5-F >31.6 1.5 0.37
17 CHO 4′-Cl Ph 5-F >31.6 9.09 0.29
18 CHO 4′-Cl Ph 6-F >31.6 9.19 0.12
19 CHO 4′-Cl Ph 5-Cl >31.6 10 0.4
20 CHO 4′-Cl Ph 6-Br 21 32 0.09
21 CHO 4′-Cl Ph 2-O, 6-Cl 18.6 18.2 18.2
22 CHO CH (CH3)2 H >31.6 >31.6 1.99
23 H Ph H >31.6 >31.6 >31.6
24 H 4′-Cl Ph 2-CH2OH, 5-F 17.4 15.1 11.5
25 CN 3′-Cl Ph H >31.6 >31.6 >31.6
26 COCH3 Ph H >31.6 >31.6 10
27 COCH3 2′-Cl Ph H >31.6 >31.6 >31.6
28 COCH3 3′-Cl Ph H >31.6 >31.6 >31.6
29 COCH3 4′-Cl Ph H >31.6 >31.6 >31.6
30 CH2OH Ph H 14.5 0.03 0.112
31 CH2OH 3′-F Ph H >31.6 0.02 0.04
32 CH2OH 4′-F Ph H 17.0 0.03 0.118
33 CH2OH 2′-Cl Ph H >31.6 2.51 0.10
34 CH2OH 3′-Cl Ph H >31.6 0.16 0.019
35 CH2OH 4′-Cl Ph H >31.6 0.079 0.016
36 CH2OH 3′-Br Ph H >31.6 0.032 0.028
37 CH2OH 4′-Br Ph H >31.6 0.39 0.031
38 CH2OH 3′-I Ph H >31.6 0.02 0.1
39 CH2OH 3′-CF3 Ph H >31.6 0.56 0.039
40 CH2OH 4′-CF3 Ph H >31.6 1.25 1.25
41 CH2OH 3′-Me Ph H >31.6 1.00 0.031
42 CH2OH 4′-Me Ph H >31.6) 0.15 0.031
43 CH2OH 3′-NO2 Ph H >31.6 0.39 0.039
44 CH2OH 4′-NO2 Ph H >31.6 0.15 0.079
45 CH2OH 4′-OMe Ph H >31.6 0.063 0.079
46 CH2OH 2′,4′-2Cl Ph H >31.6 1.58 0.079
47 CH2OH 3′,4′-2Cl Ph H >31.6 0.31 0.031
48 CH2OH 3′,4′-2Br Ph H >31.6 0.10 0.05
49 CH2OH H 5-F >31.6 13.8 16.9
50 CH2OH 3′-F Ph 5-Cl 10.0 0.16 0.07
51 CH2OH 4′-Cl Ph 5-F 8.12 0.08 0.03
52 CH2OH 4′-Cl Ph 6-F >31.6 1.00 0.45
53 CH2OH 4′-Cl Ph 5-Cl >31.6 13.0 5.75
54 CH2OH 4′-Cl Ph 5-OMe >31.6 12.5 1.51
55 CH2OH 4′-Me Ph 5-F 11.7 0.03 0.01
56 CH2CH2OH 4′-Cl Ph H >31.6 >31.6 >31.6
57 CH2CH2CH2OH Ph H >31.6 >31.6 >31.6
58 C(OH)HCH3 4′-Cl Ph H >31.5 19.9 25.1
59 CH2OCH3 4′-Cl Ph H >31.6 7.94 1.99
60 graphic file with name nihms285028t1.jpg 4′-Cl Ph H >31.6 0.063 0.039
61 graphic file with name nihms285028t2.jpg 4′-Cl Ph H >31.6 0.2 0.02
62 COOH Ph H >31.6 >31.6 >31.6
63 COOH 4′-Cl Ph H >31.6 >31.6 >31.6
64 COOCH3 4′-Cl Ph H 17.7 25.1 31.6
65 COOCH3 4′-Br Ph H 5.00 6.30 5.00
66 CH3 4′-Cl Ph H >31.6 >31.6 >31.6
67 graphic file with name nihms285028t3.jpg 4′-Cl Ph H 31.6 5.01 0.10
68 graphic file with name nihms285028t4.jpg 3′-Cl Ph >31.6 >31.6 >31.6
69 graphic file with name nihms285028t5.jpg 3′-Br Ph >31.6 >31.6 >31.6