Synthesis of some hetaryl substituted benzofurans of potential antitumor activity

ABSTRACT

Acetyl-benzo [b] furan [1] reacts with DMF - DMA to give the novel 1-[benzofuran-2-yl]-3-[dimethylamino rpropen-2-one [2]. The reaction of the latter with hydroxylamim or hydrazine hydrate furnished 5- [benzofuran-2-yl]-isoxazole [3] and 3-[benzofuran-2-yl]-1 H-pyrazole [4], respectively. Also. reaction of2 with various active methylene compounds and hydrazonoyl halides afforded regioselectively the respective 2,3.6- trisllbstituted pyridine [Sa-c] and [pyrazol-4-yl]methanones [10a-t]. respectively. Also. reaction of 10 with hydrazine hydrate afforded the corresponding pyrazolopyriúlazines [II a-c]. Preliminary screening for the antitumor activity of the synthtsized compounds against the liver carcinoma cell line HEPG-2 has been carried out. The results revealed that the compounds 3. 4 and 13b showed high degree of activity. while the other compounds showed low activity