Abstract

Chalcone analogues of established anti-cancer molecules such as Colchicine and Combretastatin A-4 have been shown to be effective inhibitors of microtubule polymerization in rapidly dividing cancer cells. In addition, this group of molecules exhibit high solubility in water, high potency to malignant cells, and are often cheaper to synthesize and less harmful to the non-malignant tissue that surrounds cancerous growths. In an effort to produce chalcone analogues of Combretastatin A-4, various azidochalcones will be thermolized to produce a phenstatin analogue, which belongs to a group of well-known anti-cancer molecules that exhibit similar cytotoxic properties to chalcones. The resultant molecules will be examined for water solubility and cytotoxicity. Past research has shown that, when thermolized, the azidochalcone tends to form a cyanochalcone instead of the desired phenstatin analogue. The aim of this research is to examine the substitution of the rings to see if assorted chemical groups have an effect on desired phenstatin synthesis. In addition, the research will help to determine the reaction mechanism and see what role the substituents play in the mechanistic process. New procedures will be examined to determine if more pure products and greater percent yields can be established by evaluating the various substituents off the main ring of the molecules. Successful bromination of 3’-methoxyacetophenone and 3’,4’,5’- trimethoxyacetophenone has occurred, as well as a successful azide substitution of 2-bromo-3’-methoxyacetophenone and 2-bromo-3’,4’,5’- trimethoxyacetophenone.

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