Thesis (M.Sc.) - Cairo University - Faculty of Science - Department of Organic Chemistry

A series of new chalcones was prepared by reaction of ethyl 3-acetyl-1-aryl-5-methyl-1H-pyrazole-4-carboxylate with a number of substituted benzaldehyde in ethanol in the presence of a catalytic amount of sodium hydroxide. One of these chalcones was used as a building block for constructing a pyrazoline ring via its reaction with thiosemicarbazide in ethanol containing sodium hydroxide as basic catalyst. The produced compound was used for preparation of two series of thiazole derivatives by its reaction with a number of hydrazonoyl chlorides in dioxane under reflux in the presence of triethylamine as basic catalyst. Moreover, reaction of 3-acetylpyrazole thiosemicarbazone derivative with a number of N-aryl-2-oxopropane hydrazonoyl chlorides in dioxane in the presence of triethylamine afforded 5-arylazothiazole derivatives. Also, reaction of ethyl 3-acetyl-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate with terephthaldehyde in ethanol in the presence of sodium hydroxide at room temperature furnished novel bis-chalcone incorporating two pyrazole rings. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. In addition, some of the newly synthesized chalcones were tested for their cytotoxicity against human colon carcinoma cell line (HCT-116) and the results revealed that some compounds have promising activities compared with the standard drug Doxorubicin. Molecular docking was also carried out for the high potent compounds

Issued also as CD