Date Approved
8-22-2019
Embargo Period
8-22-2019
Document Type
Thesis
Degree Name
M.S. Pharmaceutical Sciences
Department
Chemistry & Biochemistry
College
College of Science & Mathematics
Advisor
Jonnalagadda, Subash
Committee Member 1
Mugweru, Amos
Committee Member 2
Ramanujachary, Kandalam
Keywords
Baylis-Hillman reaction, anti-cancer agents
Subject(s)
Betulin; Drug development
Disciplines
Medicinal and Pharmaceutical Chemistry
Abstract
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.
Recommended Citation
Kommineni, Sai Krishna, "Synthesis of betulinic acid via Baylis-Hillman reaction" (2019). Theses and Dissertations. 2731.
https://rdw.rowan.edu/etd/2731