Synthesis of 1,5-diaryl-1-penten-3-one and 1,5-diaryl-2-penten-1-on structured compounds

In this work, twelve 1,5-diaryl-1-penten-3-one and two 1,5-diaryl-2-penten-1-one structured compounds were synthesized. In-situ enamination of 4-phenyl-2-butanone or 4-(4-hydroxyphenyl)-2-butanone with pyrrolidine and acetic acid and then treatment with benzaldehydes gave the corresponding 1,5-diaryl-1-penten-3-one structured compounds. Wittig condensation of phosphorane prepared from 2-bromo-acetophenone with 3-phenylpropanal and 3-(4-methoxyphenyl)propanal afforded the corresponding 1,5-diaryl-2-penten-1-one. 1,5-diaryl-1-penten-3-one were tested against glioblastoma (U87-MG), breast cancer (MCF-7), prostate carcinoma (PC-3) tumor cell lines and showed considerable cytotoxic activity against especially MCF-7 cell lines.