M.S. Pharmaceutical Sciences
Chemistry & Biochemistry
College of Science & Mathematics
Committee Member 1
Committee Member 2
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.
Kommineni, Sai Krishna, "Synthesis of betulinic acid via Baylis-Hillman reaction" (2019). Theses and Dissertations. 2731.