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 pyrazolopyriú:lazines [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
Subject(s)
Antineoplastic Agents/chemistry , Cytotoxins/chemical synthesis , Carcinoma, Hepatocellular/therapyABSTRACT
New series of coumarin derivatives was synthesized and evaluated as antitumor agents against breast cancer in human cell line [MCF 7]. The key compound 8-acetyl-7-hydroxy-4-methyl coumarin [1] was synthesized and condensed with phenyl hydrazine to form the hydrazone derivative 2. Also, 1 condensed with different alkylating agents to give the corresponding sulphonyl derivatives 3a, b which further condensed with 2,4-dinitrophenyihydrazine to give the corresponding hydrazones 4a,b. One pot reaction of 5 with different aldehydes, ethylcyanoacetate and ammoniumacetate gave pyridone derivatives 6a-e. Also. compound 5 condensed with different aldehydes then cyclized to give the pyrazoline derivatives 9a,b and 10a,b. While, on condensation of 5 with thiosemicarbazide derivatives followed by cyclization the resulting product, gave the oxathiazoline 12 and thiazolidine 13. Some of these newly synthesized compounds showed noderate activity against breast carcinoma cell line[MCF7] in human