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The synthesis of anti-cancer Brassica glucosinolates, dihydrothiazines and derivatives.

Lucas, Robert Anthony. (2003) The synthesis of anti-cancer Brassica glucosinolates, dihydrothiazines and derivatives. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

Glucosinolates and isothiocyanates have been known to possess anti-cancer properties. Harvesting these materials from cruciferous vegetables is problematic, the isothiocyanate is reactive and susceptible to hydrolysis, and the glucosinolate cleaves to give glucose and the isothiocyanate in the presence of the enzyme myrosinase (found within the plant). Therefore it would be useful if we were able to synthesise these materials. Synthesising isothiocyanates with increased potency regarding their anti-cancer properties would also be sagacious. Dihydrothiazines are useful precursors to sulfinic esters, which in turn have the potential to be converted into chirally pure isothiocyanates. Synthesis of the glucosinolate glucoraphanin, dihydrothiazines and derivatives are discussed within this thesis. Synthesis of the glucosinolates proved to be far more difficult than first expected. A simple model compound (methyl glucosinolate) was synthesised, however, the glucoraphanin proved to be problematic. Reported is a method that traps the oxime intermediate enabling successful synthesis of the hydroximate, precursor to the glucosinolate. A series of new dihydrothiazines have been successfully synthesised. This portion of work has developed a novel synthetic procedure for their synthesis allowing three reactions to be performed in the one reaction apparatus. The result of this is to provide an efficient route to the dihydrothiazines. The syntheses of an epoxide, allylic alcohol and sulfone dihydrothiazine derivatives are reported within this thesis in addition to the synthesis of sulfinic esters. It was also observed that it is possible for the dihydrothiazine to degrade through two separate hydrolysis routes depending on the environment it experiences.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Lucas, Robert Anthony.UNSPECIFIEDUNSPECIFIED
Date : 2003
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THSUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Depositing User : EPrints Services
Date Deposited : 09 Nov 2017 12:18
Last Modified : 09 Nov 2017 14:47
URI: http://epubs.surrey.ac.uk/id/eprint/844420

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