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Chiral alkaloid derivatives: Synthesis and medicinal chemistry applications

Canning, Daniel (2011) Chiral alkaloid derivatives: Synthesis and medicinal chemistry applications. PhD thesis, Dublin City University.

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Abstract

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.

Item Type:Thesis (PhD)
Date of Award:November 2011
Refereed:No
Supervisor(s):Gathergood, Nicholas
Uncontrolled Keywords:novel opioid alkaloids; codeine; morphine
Subjects:Physical Sciences > Organic chemistry
Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Research Initiatives and Centres > National Institute for Cellular Biotechnology (NICB)
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
Funders:IRCSET PHD Scholarship
ID Code:16324
Deposited On:30 Nov 2011 11:01 by Nick Gathergood. Last Modified 11 Jan 2013 14:22

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