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Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols.

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Amewu, Richard, Gibbons, Peter, Mukhtar, Amira, Stachulski, Andrew V., Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192, Hall, Charlotte, Rimmer, Karen, Davies, Jill, Vivas, Livia, Bacsa, John, Mercer, Amy E., Nixon, Gemma, Stocks, Paul A. and O'Neill, Paul M. (2010) 'Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols.'. Organic & biomolecular chemistry, Vol 8, Issue 9, pp. 2068-77.

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Abstract

Thiol-Olefin Co-Oxygenation (TOCO) methodology has been applied to the synthesis of a small library of weak base and polar 1,2,4-trioxanes. The 1,2,4-trioxane units synthesised exhibit remarkable stability as they survive base catalysed hydrolysis and mixed anhydride/amine coupling reactions. This unique stability feature has enabled a range of novel substitution patterns to be incorporated within the spiro 1,2,4-trioxane unit. Selected analogues express potent in vitro nM antimalarial activity, low cytotoxicity and oral activity in the Plasmodium berghei mouse model of malaria.

Item Type: Article
Additional Information: Article acceptance date: 4th February 2010
Subjects: QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials
WC Communicable Diseases > Tropical and Parasitic Diseases > WC 770 Therapy
Faculty: Department: Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group
Digital Object Identifer (DOI): https://doi.org/10.1039/b924319d
Depositing User: Mary Creegan
Date Deposited: 31 Aug 2010 10:46
Last Modified: 17 Jul 2020 10:57
URI: https://archive.lstmed.ac.uk/id/eprint/1018

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