Date of Award

2013

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Franks, Dr. Marion A.

Abstract

The goal of this project was the synthesis of 4-substitued coumarins and 2H-chromene-2-thione derivatives that can be used to inhibit or retard the growth of cancer cells. According to the American Cancer Society's 2012 death statistics for prostate cancer, 28,170 men died from prostate cancer and there was 241,740 (29%) new cases of prostate cancer as well (Society, 2012). Few studies have been conducted on 2H-chromene-2-thiones and their ability to act as cancer chemopreventive or anticancer agents, therefore, we seek to synthesize a sequence of coumarins and 2H-chromene-2-thiones via the Von Pechmann reaction. We believe that the 2H chromene-2-thiones will exhibit better chemopreventive activity then the analogous coumarins because of the presence of the softer sulfur atom. The syntheses of the coumarin derivatives in this study were accomplished using green chemistry. The indium chloride catalyzed Von Pechmann condensation required no solvent and formed coumarins efficiently. Upon synthesizing coumarins, they were converted into their 2H-chromene-2-thione analogs using Lawesson's reagent. Percent yields of the coumarin derivatives range from 40% to 80%. The 2H chromene-2-thione percent yields range from 11% to 61%.

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