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Abstract The reaction of cyclohexan-1,3-dione (1) with benzaldhyde, 4-chlorobenzaldhyde and 4-methoxy benzaldhyde (2a-c) in ethanol in the presence of catalytic amount of piperidine afforded 2-Arylidencyclohexan-1,3-dione 3a-c. The latter compounds reacted with elemental sulfer and either of malonanitrile (4a) or ethyl cyanoacetate (4b) in 1,4-dioxan in the presence of triethylamine to give tetrahydrobenzo[b]thiophen-5-one derivatives 5a-f. Compounds 5a, b were used for the synthesis of thiophene, thiazole and isoxazale derivatives through their reactions with different chemical reagents. The analytical and spectral data of newly synthesized compounds were consistent with their respective structures. The anti-proliferative activities of the newly synthesized compounds were evaluated against the six cancer cell lines A549, HT-29, MKN-45, U87MG, SMMC-7721 and H460. The most potent compounds toward the cancer cell lines 3a, 3c, 5d, 7c, 11c, 16a, 16c, 17a, 19f, 20a, 21c, 23a and 23c, were further investigated towards the five tyrosine kinases c-kit, FIT-3, VEGFR-2, EGFR and PDGFR. Compounds 3c, 5d, 16c, 17a, 19f and 21c were selected for testing of their inhibition for the Pim-1 kinase due to their anti-proliferation activities against the cancer cell lines and their high activities against the tyrosine kinases |