Chiang Mai Journal of Science

We now focus on the synthesis of curcumin analogues (1-8) bearing -OCH3/-OH/-F substituents on the phenyl rings via base-catalyzed aldol condensations between various benzaldehydes with pentane- 2,4-dione. The analogues were subsequently tested for in vitro anticancer capacity against human lung cancer cell line (LU-1) by determining their half-maximal inhibitory concentration (IC50, μM). The presence of methoxy/hydroxy groups at meta-positions in aromatic rings of compounds (3, IC50 = 29.21±2.12 μM; 5, IC50 = 68.69±5.47 μM) exhibited higher anticancer activities, whereas analogues (2, 4) having similar substituents at para-positions displayed very poor activities when compared with curcumin (1, IC50 = 72.88±6.19 μM). Fluorinated curcuminoids (6, 7) showed inactivities. Remarkably, the level of inhibition of (8) containing 3-fluoro aromatic moiety was improved with an IC50 of 56.39±4.26 μM in this assay. The results indicated that the 3-substituted phenyl motifs are responsible for inhibition of LU-1 cell growth.