Date Approved
3-15-2018
Embargo Period
3-19-2018
Document Type
Thesis
Degree Name
MS Pharmaceutical Sciences
Department
Chemistry and Biochemistry
College
College of Science & Mathematics
Advisor
Jonnalagadda, Subash
Committee Member 1
Ramanujachary, Kandalam
Committee Member 2
Wu, Chun
Keywords
boronic acids, benzoboroxoles, anti-cancer agents
Subject(s)
Drug development
Disciplines
Medicinal and Pharmaceutical Chemistry
Abstract
Boronic acids are a promising class of compounds due to their wide range of applications in medicinal and materials chemistry, and as coupling agents in organic synthesis. B-hydroxy-1,2-oxaborolanes (benzoboroxoles) are categorized as cyclic boronic acid derivatives and they are very important organic molecules because of their metabolic stability and their ability to undergo important C-C bond forming reactions such as Suzuki cross coupling. Several of these cyclic boronic acids are found to have promising pharmacological properties as antifungal, antimalarial and anti-inflammatory agents. However, based on the literature reports, synthesis of highly functionalized benzoboroxoles is typically cumbersome and not very conducive for large-scale synthesis.
This thesis details our efforts on the development of novel synthetic methodologies for the synthesis of functionalized benzoboroxoles as potential therapeutic agents. We initiated the synthesis of novel benzoboroxoles starting from 2-formylphenylboronic acid employing reactions such as Baylis-Hillman reaction, Passerini reaction, aldol reaction, and reductive amination. Further functionalization of these benzoboroxoles was achieved via nitrosation and amidation protocols. The biological evaluation of these synthetic derivatives showed excellent promise as anti-cancer agents.
Recommended Citation
Patel, Bhawankumar Pravinchandra, "Novel aminobenzoboroxoles as potential anti-cancer agents" (2018). Theses and Dissertations. 2527.
https://rdw.rowan.edu/etd/2527