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An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity

Ellis, Gemma L., Amewu, R., Hall, Charlotte, Rimmer, Karen, Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192 and O'Neill, Paul M. (2008) 'An efficient route into synthetically challenging bridged achiral 1,2,4,5-tetraoxanes with antimalarial activity'. Bioorganic & Medicinal Chemistry Letters, Vol 18, Issue 5, pp. 1720-1724.

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Abstract

Here we present an efficient route into synthetically challenging bridged 1,2,4,5-tetraoxanes. The key to the success of this route is the use of H2O2 and catalytic I-2 to form the gem-dihydroperoxide followed by a Ag2O mediated alkylation using 1,3-diiodopropane. Using this methodology a range of bridged tetraoxanes which display good in vitro antimalarial activity were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: antimalarial artemisinin 1,2,4-trioxane tetraoxane plasmodium falciparum crystal-structure en-route artemisinin peroxides dispiro-1,2,4,5-tetraoxanes analogs spiro-1,2,4,5-tetraoxacycloalkanes dispiro-1,2,4-trioxolanes tetraoxanes derivatives
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/10.1016/j.bmcl.2008.01.053
Depositing User: Mary Creegan
Date Deposited: 13 Aug 2010 09:15
Last Modified: 06 Feb 2018 13:00
URI: http://archive.lstmed.ac.uk/id/eprint/772

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