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

First Advisor

Jonnalagadda, Subash

Second Advisor

Ramanujachary, Kandalam

Third Advisor

Wu, Chun

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.

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