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Design and synthesis of orally active dispiro 1,2,4,5-tetraoxanes; synthetic antimalarials with superior activity to artemisinin

Amewu, R., Stachulski, A. V., Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192, Berry, N. G., Bray, Patrick, Davies, Jill, Labat, G., Vivas, L. and O'Neill, P. M. (2006) 'Design and synthesis of orally active dispiro 1,2,4,5-tetraoxanes; synthetic antimalarials with superior activity to artemisinin'. Organic & Biomolecular Chemistry, Vol 4, Issue 24, pp. 4431-4436.

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Abstract

Unsymmetrical dispiro- and spirotetraoxanes have been designed and synthesized via acid-catalyzed cyclocondensation of bis(hydroperoxides) with ketones. Incorporation of water-soluble and polar functionalities, via reductive amination and amide bond formation, produces several analogues with low nanomolar in vitro antimalarial activity. Several analogues display an unprecedented level of oral antimalarial activity for this class of endoperoxide drug.

Item Type: Article
Uncontrolled Keywords: antiproliferative activity qinghaosu artemisinin cyclic peroxides dispiro-1,2,4,5-tetraoxanes 1,2,4,5-tetroxanes drug 1,2,4,5,7-pentoxocanes decomposition tetraoxanes derivatives
Subjects: QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials
QV Pharmacology > QV 34 Experimental pharmacology (General)
Faculty: Department: Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group
Digital Object Identifer (DOI): https://doi.org/10.1039/b613565j
Depositing User: Julia Martin
Date Deposited: 25 Oct 2010 11:12
Last Modified: 06 Feb 2018 13:01
URI: http://archive.lstmed.ac.uk/id/eprint/1440

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