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. Author manuscript; available in PMC: 2016 Apr 1.
Published in final edited form as: Bioorg Med Chem. 2015 Feb 13;23(7):1507–1514. doi: 10.1016/j.bmc.2015.02.003

Table 1.

Structures of curcumin derivatives

graphic file with name nihms-663940-t0002.jpg Effects on
EGFR
expressiona
Cmpd R1 R2 R3 R4 R5 R6 R7 R8 R9 R10 R11 CL1-5 H1975
1 H Me H H H H OMe H H H H + +
2 H Me Me H H H OMe Me H H H + +++
3 H Me H H H H OMe H H H (CH2)2CO2Et + −
4 H Me Me H H H OMe Me H H CH=CHCO2Et − −
5 H Me H H H H OMe Me H H H + +
6 H Me H H H H H H H H H − −
7 graphic file with name nihms-663940-t0003.jpg − −
8 OMe Me Me H H OMe OMe Me H H H + +
9 H Me Me H OMe H OMe Me H OMe H + +
10 H Me Me H H H OH Me H H H + ++
11 OMe Me Me H H H OMe Me H H H + +
12 H Me Me H OMe H OMe Me H H H + ++
13 H Me H H H H OMe Me H H (CH2)2CO2Et + ++
14 H Me H H H H OMe H H H COMe + +
15 H Me Me H H H OMe Me H H Me + +
16 H Me H H H H OH H H H H − ++
17 H H H H H H OMe H H H (CH2)2CO2Et + +
18 H Me H H H H OMe H H H CH=CHCO2Et − −
19 H Me H H H H OMe H H H (CH2)2CO2H − −
20 H Me CH2CO2Me H H H OMe CH2CO2Me H H H − −
21 H Me CH2CO2Me H H H OMe CH2CO2Me H H (CH2)2CO2Et − −
22 H H H H H H OH H H H (CH2)2CO2Et + −
23 H H H H H H OH H H H H + + b
24 H H H H H H OH H H H (CH2)2CO2H − −
25 H H H H H H OMe H H H (CH2)2CO2H − −
26 H Me H H H H OH H H H CH=CHCO2Et − −
27 H Me CH2CO2H H H H OMe CH2CO2H H H H − −
28 H Me CH2CONHPh H H H OMe CH2CONHPh H H H − −
29 H Me (CH2)3CO2Et H H H OMe (CH2)3CO2Et H H H − −
30 H Me (CH2)3CO2H H H H OMe (CH2)3CO2H H H H − −
31 H Me (CH2)3CO2Et H H H OMe (CH2)3CO2Et H H (CH2)2CO2Et − −
32 H Me (CH2)3CO2H H H H OMe (CH2)3CO2H H H (CH2)2CO2H − −
33 H Me Me H H H OMe Me H H (CH2)2CO2Et − −
34 H Me Me OH H H OMe Me OH H (CH2)2CO2Et + b +
35 H Me H OMe H H OMe H OMe H (CH2)2CO2Et − −
36 H Me Me H F H OMe Me H F H + ++
37 H Me Me OH H H OMe Me OH H H − −
a

Effects of compounds on EGFR expression in H1975 cells can be ranked as negative (−), + (good), ++ (better), or +++ (best), while effects in CL1-5 cells can be observed “all (+) or none (−)” based on our analysis.

b

EGFR was not affected, pEGFR was reduced.