17 research outputs found
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Development of new methodologies for entry to targets of therapeutic interest
This Account provides an overview of strategies that have been reported from our laboratories for the synthesis of targets of therapeutic interest, namely carbohydrates, and prodrugs for the treatment of melanoma. These programmes have involved the development of new synthetic methodologies including the regio- and stereoselective synthesis of specific carbohydrate isomers, and new protecting group methodologies. This review provides an insight into the progress of these research themes, and suggests some applications for the targets that are currently being explored
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Synthetic entry to functionalised morpholines and [1,4]-oxazepanes via reductive amination reactions of carbohydrate derived dialdehydes
The rapid synthesis of functionalised morpholines and [1,4]-oxazepanes displaying up to three stereocentres, by reductive amination reactions between carbohydrate derived dialdehydes and a range of amines, is described. (C) 2004 Elsevier Ltd. All rights reserved
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Application of the asymmetric hetero Diels-Alder reaction for synthesising carbohydrate derivatives and glycosidase inhibitors
This review provides a discussion of recent developments in the asymmetric hetero Diels-Alder reaction (AHDAR), with particular emphasis on the synthesis of carbohydrates, their derivatives, and inhibitors of carbohydrate processing enzymes
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A new entry to 4,6-O-benzylidene glucal from phenyl 1-seleno-alpha-D-mannopyranoside
The two-step synthesis of 4,6-O-benzylidene glucal, in 59% overall yield, from phenyl 1-seleno-alpha-D-mannopyranoside is described. (c) 2005 Elsevier Ltd. All rights reserved
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Preparation of enantiopure long chain threo-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids
The synthetic approach to threo-2-amino-3-hydroxyesters possessing long alkyl chains outlined herein centres on the generation of chiral azomethine ylids by reaction of (5R)-5-phenyl-morpholin-2-one, (R)-(1), with long chain aldehydes. In the presence of a second equivalent of aldehyde, the azomethine ylid can be trapped to afford a cycloadduct with three new stereodefined centres. Degradation of the cycloadduct allows entry to beta-substituted-alpha-amino acid derivatives, which have potential as building blocks for sphingosine synthesis
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Fighting skin cancer with prodrugs
Excessive exposure to uv light initiates melanoma in the skin. Tumour-specific enzymes are hijacked to deliver anticancer drugs
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New prodrugs derived from 6-aminodopamine and 4-aminophenol as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)
Two novel tyrosinase mediated drug delivery pathways have been investigated for the selective delivery of cytotoxic units to melanocytes from urea and thiourea prodrugs. The synthesis of these prodrugs is reported, as well as oximetry data that illustrate that the targets are substrates for tyrosinase. The stability of each of the prodrugs in (i) phosphate buffer and (ii) bovine serum is discussed, and the urea prodrugs are identified as lead candidates for further studies. Finally, HPLC studies and preliminary cytotoxicity studies in a melanotic and an amelanotic cell line, that illustrate the feasibility of the approach, are presented