Thesis (Ph.D.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The 1-(1H-benzo[d]imidazol-2-yl)propan-2-one (3) and the ethyl 2-(1Hbenzo[ d]imidazol-2-yl)acetate (16) were used as the key starting material which reacted with salicylaldehyde to give the corresponding benzo[4,5]imidazo[1,2-a]quinoline derivatives. On the other hand, both of them were reacted with different reagents to give thiophene, pyran and benzo[4,5]imidazo[1,2-c]pyrimidine derivatives. The synthesized compounds were evaluated against the six cancer cell linesA549, HT-29, MKN-45, U87MG, and SMMC-7721 and H460 using the standard MTT assay in vitro, with foretinib as the positive control, many compounds expressed high inhibitions. Compounds 3, 5b, 10b, 12a, 12b, 16, 18, 19a, 19b and 21 were the most cytotoxic compounds toward the six cancer cell lines This work demonstrated multicomponent reactions of cyclohexan-1,3- dione with aromatic aldehydes and diethylmalonate to give the the 7,8- dihydro-4H-chromen-5(6H)-one derivatives 4a-c). The reaction of compounds 4a-c with either of hydrazine hydrate of phenylhydrazine gave the chromeno[2,3-c]pyrazole derivatives 5a-f, respectively. In addition further heterocyclization reactions were adopted to give the chromeno[3,2- d]isoxazole, chromene-3-carboxamide derivatives. Moreover, the multicomponent reaction of cyclohexan-1,3-dione (1) with either of aromatic

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