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Chiral alkaloid derivatives: Synthesis and medicinal chemistry applications
Canning, Daniel
The preparation of a selection of novel opioid alkaloids based on alteration at the 1, 3 and 6 positions of codeine and morphine has been achieved. Herein we present the synthetic methodology, structural characterisation and biological evaluation of these novel opioid species. A range of opioid derivatives with modification at the 6 position to form linked bis-opioid species were successfully synthesised. The derived compounds contain both ester and ether linked moieties. A selection of derivatives with modification at the 1 position of codeine were also generated through Heck, Stille and Suzuki palladium catalysed carbon-carbon coupling. A combination of both synthetic approaches has led to a variety of opioid species with modification at both the 1 and 6 positions. A selection of the opioid species generated were analysed for their binding affinity to the mu opioid receptor through radioligand binding techniques. Binding affinities of a variety of the opioid species to a selection of metals were also assessed by metal picrate extraction studies.
Keyword(s): Organic chemistry; Chemistry; novel opioid alkaloids; codeine; morphine
Publication Date:
2011
Type: Other
Peer-Reviewed: Unknown
Language(s): English
Contributor(s): Gathergood, Nicholas
Institution: Dublin City University
Citation(s): Canning, Daniel (2011) Chiral alkaloid derivatives: Synthesis and medicinal chemistry applications. PhD thesis, Dublin City University.
Publisher(s): Dublin City University. School of Chemical Sciences; Dublin City University. National Institute for Cellular Biotechnology (NICB)
File Format(s): application/pdf
Related Link(s): http://doras.dcu.ie/16324/1/Thesis_FINAL_Draft_09-05-11.pdf
First Indexed: 2014-04-17 05:43:35 Last Updated: 2019-02-09 06:49:11