Date of Award

2013

Document Type

Thesis

First Advisor

Franks, Dr. Marion A.

Abstract

Carcinogenesis is the transformation of a normal cell into a cancerous cell. Cancer chemoprevention is the use of natural and synthetic compounds to stop carcinogenesis. These compounds have been labeled chemopreventives and they take advantage of the human body’s natural defenses to stop carcinogenesis. Chalcones have demonstrated antibacterial, antifungal, antitumor, and anti-inflammatory properties. In this project, chalcones and their derivatives are synthesized with the goal to be used as possible chemopreventives. We believe that when tested on cancer cell lines, the boronic acid derivative will show greater chemopreventive activity because of the boronic acid’s increased bioavailability. We have synthesized and characterized a series of methoxy and boronic acid chalcones via adol condensation. Our synthetic methodology included the conversion of hydroxybenzaldehydes into alkoxybenzaldehydes via Williamson Ether Synthesis, followed by a Clasien-Schmidt condensation between the alkoxybenzaldehydes and an acetophenone. The synthesized chalcones were characterized 1 H, 13 C, and 2D NMR spectroscopy and were shown to exhibit yields ranging from 58% to 91%.

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