Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.518909
Title: Studies on ring closure heterometathesis and the synthesis of novel glycosidase inhibitors
Author: Maxwell, Vanessa L.
Awarding Body: University of Leicester
Current Institution: University of Leicester
Date of Award: 2005
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Abstract:
Compound I was synthesised to study intramolecular ring closing metathesis of an oxime and an olefin. In the event an intermolecular reaction took place to give II. (Fig. 11160A).;A series of bias imines IV were synthesised and also subjected to ring closure metathesis conditions using the Grubbs catalyst. No cyclisation was observed. (Fig. 11160B).;Three diamino sugar derivatives V were prepared by epoxide opening of the corresponding 2,3 manno (up) epoxide. Benzylidene deprotection was not possible. (Fig. 11160C).;A further six examples of deprotected diamino altro derivatives 395b-g were prepared and tested for glycosidase inhibition and the best results were obtained when n = 4 and n = 5 where IC50 values gave 0.15 mM and 0.63 mM respectively for beta-galactosidase from bovine liver. Nine examples of the benzylamino altro derivatives were prepared and tested for glycosidase inhibition. IC50 values obtained gave 70 microM and 90 microM where n = 3, R = H and n = 4, R = H respectively for beta-galactosidase from bovine liver. (Fig. 11160D).;Opening the manno epoxide produced seven examples and the structure of the products were proved with an X-ray structure where R = morpholine. The stereochemistries of the other examples were assigned following 13 C comparison. By contrast opening of the allo epoxide gave attack at C-3 and this fact was determined by an X-ray structure on R = furanyl. 13C comparison indicated that the other examples had followed attack at C-3.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.518909  DOI: Not available
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