Synthesis of Curcumin Analogue, N-H and N-Benzil-4-Piperidone and their Cytotoxic Activity

Abstract

Four piperidone curcumin analogues, N-H-(3E,5E)-3,5-bis-(2,4,5-trimethoxybenzaldehyde)-4-piperidone (A1), N-H-(3E,5E)-3,5-bis-(3,4,5-trimethoxy benzaldehyde)-4-piperidone (A2), N-benzil-(3E,5E)-3,5-bis-(2,4,5- trimethoxybenzaldehyde)-4-piperidone (A3) and N-benzil-(3E,5E)-3,5-bis-(3,4,5-trimethoxybenzaldehyde)-4-piperidone) (A4) were synthesized from N-H-4-piperidone and N-benzil-4-piperidone with 2,4,5-trimethoxybenzaldehyde and 3,4,5-trimethoxybenzaldehyde. The Claisen-Schmidt condensation reaction was used in alkali condition with combinatorial approach. The compounds showed red brick crystal, yellow powder, brown powder, and light yellow powder with the yield of 88.8%, 44.5%, 84.7%, and 53.0% respectively. All structure of the compounds were confirmed by using UV, IR, 13C-NMR, 1H-NMR and mass spectroscopy. Cytotoxic activity against P-388 murine leukemia cell showed various IC50 values of >100, 92.62, 0.49 and 67.04μg/mL, respectively.