Synthesis and biological evaluation of functionalized benzoxaboroles as potential antimicrobial agents
2012-10
Loading...
View/Download File
Persistent link to this item
Statistics
View StatisticsJournal Title
Journal ISSN
Volume Title
Title
Synthesis and biological evaluation of functionalized benzoxaboroles as potential antimicrobial agents
Authors
Published Date
2012-10
Publisher
Type
Thesis or Dissertation
Abstract
Boronic acids are extremely valuable compounds that have applications in
medicinal, and materials chemistry, and also as cross-coupling agents in synthetic
chemistry. Boronic acids often function as inhibitors for various enzymes due to their
unique electronic and physicochemical properties. B-hydroxy-1,2-oxaborolanes
(benzoboroxoles) are a class of cyclic boronic acid derivatives and are highly important
organic synthons because of their structural 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 possess excellent pharmacological properties as
antifungal, antimalarial and anti-inflammatory agents. However, the existing literature
methodologies for the synthesis of highly functionalized benzoboroxoles are difficult and
often are not suitable for large scale synthesis.
We have been working on the development of novel synthetic methodologies for
the synthesis of functionalized benzoxaboroles as potential therapeutic agents.
Previously, we have synthesized several benzoxaboroles employing Baylis-Hillman,
Barbier allylation, and Passerini reaction protocols. In continuation of our interest on the
development of structurally diverse benzoboroxoles, we synthesized several novel
derivatives starting from 2-formylphenylboronic acid utilizing aldol reaction as the key
step. Our studies in this area including the synthesis and structural characterization data
will be presented.
Keywords
Description
University of Minnesota M.S. thesis. October 2012. Major: Chemistry. Advisor: Prof. Paul Kiprof. 1 computer file (PDF); iv, 61 pages, appendices I-V.
Related to
Replaces
License
Series/Report Number
Funding information
Isbn identifier
Doi identifier
Previously Published Citation
Other identifiers
Suggested citation
Walsh, Peggy Jo. (2012). Synthesis and biological evaluation of functionalized benzoxaboroles as potential antimicrobial agents. Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/140949.
Content distributed via the University Digital Conservancy may be subject to additional license and use restrictions applied by the depositor. By using these files, users agree to the Terms of Use. Materials in the UDC may contain content that is disturbing and/or harmful. For more information, please see our statement on harmful content in digital repositories.