Date of Award

2013

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Franks, Marion A. PhD

Abstract

Chemopreventives are natural or synthetic compounds that are used to stop or reverse the processes of carcinogenesis or tumorigenesis. Resveratrol (3, 5, 4’-trihydroxy-trans-stilbene) is a stilbenoid and natural phenol that is found in fruits such as grapes. In addition to antioxidant and anti-inflammatory properties, resveratrol can inhibit D-type cyclins and cyclin-dependent kinase CDK4 expression. This can also lead to inducing tumor suppressors p53 and Cdk inhibitor p21. The p53 protein is encoded by the TP53 gene and responds to cellular stresses by regulating target genes that induce cell cycle arrest, apoptosis, and DNA repair among other functions. 3-nitro-2-styryl amide derivatives contain the stilbene structure similar to resveratrol and due to this similarity will be effective chemopreventives. We have synthesized five 3-nitrostyrylamides to be tested for their chemopreventive efficacy. These compounds were synthesized using a base catalyzed condensation reaction that utilized substituted benzaldehydes and methyl 2-methyl 3 nitrobenzoate to form 3-nitro-2-styrl benzoic acids to give percent yields of 35.1-90.2%. The conversion of the 3-nitro-2-styryl benzoic acids to acid chlorides was completed using an N, N-dimethylformamide catalyzed reaction with thionyl chloride. The acid chlorides were converted to amides using N-butylamine and sodium hydroxide to give percent yields of 15.9-87.7%. The synthesized amide compounds were characterized using 1H NMR, 13C NMR, FT-IR, and HPLC.

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