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. Author manuscript; available in PMC: 2012 Jun 26.
Published in final edited form as: J Med Chem. 2011 May 19;54(12):4147–4159. doi: 10.1021/jm2002348

Table 1.

Synthesis of chalcone derivatives by Claisen-Schmidt condensation and their Nrf2 induction activity

graphic file with name nihms298141t1.jpg
Entry Chalcones Substituents on Ring A Substituents
on Ring B		 Relative fold
Changea
R1 R2 R3 R4 R5 R6 R7 R8 GCLM NQO1
1 1a H H H H H H H H 0.7 1.8
2 1b OMe H H H H H H H 3.6 3.2
3 1c H OMe H H H H H H 1.5 2.4
4 1d H H OMe H H H H H 1.9 2.8
5 1e OMe H OMe H H H H H 2.7 2.8
6 1f OMe H H H OMe H H H 2.5 1.9
7 1g OMe H H OMe H H H H 3.0 2.6
8 1h H OMe OMe H H H H H 2.3 2.5
9 1i H OMe H OMe H H H H 3.0 2.4
10 1j H OMe OMe OMe H H H H 0.7 0.7
11 1k OMe OMe OMe H H H H H 2.4 2.4
12 1l OMe H OMe H OMe H H H 3.1 1.8
13 2a H H H H H CF3 H H 5.0 5.3
14 2b OMe H H H H CF3 H H 4.5 4.6
15 2c H OMe H H H CF3 H H 5.6 4.3
16 2d H H OMe H H CF3 H H 5.4 4.6
17 2e OMe H OMe H H CF3 H H 5.4 4.5
18 2f OMe H H H OMe CF3 H H 5.7 5.3
19 2g OMe H H OMe H CF3 H H 4.4 2.7
20 2h H OMe OMe H H CF3 H H 4.3 2.7
21 2i H OMe H OMe H CF3 H H 4.0 3.7
22 2j H OMe OMe OMe H CF3 H H 3.0 3.1
23 2k OMe OMe OMe H H CF3 H H 5.4 4.1
24 2l OMe H OMe H OMe CF3 H H 4.4 4.3
25 3a H H H H H H CF3 H 3.1 2.8
26 3b OMe H H H H H CF3 H 3.9 2.9
27 3c H OMe H H H H CF3 H 4.6 3.5
28 3d H H OMe H H H CF3 H 2.7 2.8
29 3e OMe H OMe H H H CF3 H 4.6 4.0
30 3f OMe H H H OMe H CF3 H 1.8 0.6
31 3g OMe H H OMe H H CF3 H 1.8 0.8
32 3h H OMe OMe H H H CF3 H 4.1 2.9
33 3i H OMe H OMe H H CF3 H 3.8 3.9
34 3j H OMe OMe OMe H H CF3 H 1.7 0.8
35 3k OMe OMe OMe H H H CF3 H 3.6 3.2
36 3l OMe H OMe H OMe H CF3 H 1.4 0.7
37 4a H H H H H H H CF3 3.1 2.9
38 4b OMe H H H H H H CF3 4.3 5.4
39 4c H OMe H H H H H CF3 2.9 3.1
40 4d H H OMe H H H H CF3 3.5 4.6
41 4e OMe H OMe H H H H CF3 5.0 4.8
42 4f OMe H H H OMe H H CF3 1.4 0.6
43 4g OMe H H OMe H H H CF3 4.1 4.0
44 4h H OMe OMe H H H H CF3 3.5 2.7
45 4i H OMe OMe OMe H H H CF3 4.1 3.7
46 4j OMe OMe OMe H H H H CF3 4.1 3.9
47 4k OMe H OMe H OMe H H CF3 2.4 2.4
48 5a H H H H H NO2 H H 2.1 1.6
49 5b OMe H H H H NO2 H H 1.9 1.4
50 5c H OMe H H NO2 H H 2.9 2.7
51 5d H H OMe H H NO2 H H 4.6 4.3
52 5e OMe H OMe H H NO2 H H 2.7 3.3
53 5f OMe H H H OMe NO2 H H 4.1 3.7
54 5g OMe H H OMe H NO2 H H 1.7 0.7
55 5h H OMe OMe H H NO2 H H 2.3 2.7
56 5i H OMe H OMe H NO2 H H 3.4 4.1
57 5j H OMe OMe OMe H NO2 H H 1.2 0.7
58 5k OMe OMe OMe H H NO2 H H 2.9 3.3
59 5l OMe H OMe H OMe NO2 H H 2.6 2.0
DMSO 1.0 1.0
Sulforaphane 2.7 3.6
a

Data presented are representative of 3 independent experiments.

Values shown are mean ± SD of quadruplicate wells.