Date Approved

4-26-2018

Embargo Period

4-30-2018

Document Type

Thesis

Degree Name

MS Pharmaceutical Sciences

Department

Chemistry and Biochemistry

College

College of Science & Mathematics

Advisor

Jonnalagadda, Subash

Committee Member 1

Perez, Lark

Committee Member 2

Moura-Letts, Gustavo

Keywords

anti-cancer agents, birch bark, betulin, betulinic acid

Subject(s)

Betulin; Drug development

Disciplines

Pharmacy and Pharmaceutical Sciences

Abstract

Betulin and betulinic acid are complex natural compounds that can be readily extracted in high quantities from external bark of yellow and white birch trees. Birch tree is native to northern New Jersey and is also commonly available for purchase as firewood. Betulinic acid is found to exhibit very good activity against few cancer cell lines, and is relatively non-toxic to normal cells. The ready availability and selective cytotoxicity coupled with the favorable therapeutic index have made betulinic acid an attractive and promising anticancer agent. However, this molecule is almost insoluble in water and shows anti-cancer activity only on very few cell lines.

This thesis details our efforts on the development of novel synthetic methodologies for the synthesis of functionalized betulin derivatives as potential anti-cancer agents. We initiated the synthesis of betulin conjugates starting from betulinic acid employing reactions such as Baylis-Hillman reaction and click reaction. Further functionalization of these conjugates was achieved via reduction and succinylation. The cytotoxicity evaluation of these compounds showed good potential as anti-cancer agents.

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