Date Approved


Embargo Period


Document Type


Degree Name

M.S. Pharmaceutical Sciences


Chemistry & Biochemistry


College of Science & Mathematics


Jonnalagadda, Subash

Committee Member 1

Mugweru, Amos

Committee Member 2

Ramanujachary, Kandalam


Baylis-Hillman reaction, anti-cancer agents


Betulin; Drug development


Medicinal and Pharmaceutical Chemistry


Betulin is readily isolated from the bark of birch trees using simple extraction techniques and this molecule as well as its derivatives (eg. betulinic acid) exhibit impressive levels of biological activity. While it is naturally available and shows selective toxicity towards certain cancers, betulin suffers from a general lack of solubility in aqueous conditions. In this regard, we took up a project involving the synthesis of conjugates of betulin with improved solubility characteristics and we were able to identify a series of compounds that showed cytotoxicity against breast and pancreatic cancer cells.

This thesis describes our efforts on the development of betulinic acid-derived second generation candidate compounds as potential anti-cancer agents. In our previous attempts, we coupled the betulinic acid template with Baylis-Hillman reaction based cinnamamides using click reaction-derived triazoles as the linker. We wanted to further explore the structure activity relationship profile for these conjugates. Accordingly, we synthesized two series of compounds (a) by removing the triazole linker and (b) by replacing the triazole with piperazine linker. The biological evaluation of these series of compounds is underway and the data obtained from this study would pave way for further functionalization and development.