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Piperidine dispiro-1,2,4-trioxane analogues

Sabbani, S., Stocks, Paul A., Ellis, G. L., Davies, Jill, Hedenstrom, E., Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192 and O'Neill, P. M. (2008) 'Piperidine dispiro-1,2,4-trioxane analogues'. Bioorganic & Medicinal Chemistry Letters, Vol 18, Issue 21, pp. 5804-5808.

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Abstract

Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used to prepare derivatives (4-7). Several of these novel 1,2,4-trioxanes had nanomolar antimalarial activity versus the 3D7 strain of Plasmodium falciparum. Amine intermediate 3 represents a versatile derivative for the preparation of achiral arrays of trioxane analogues with antimalarial activity. (C) 2008 Elsevier Ltd. All rights reserved.

Item Type: Article
Uncontrolled Keywords: hydrogen peroxide 1,2,4-trioxane endoperoxide antimalarial mechanism of action antimalarial activity artemisinin qinghaosu peroxides chemistry drug drug resistance
Subjects: WA Public Health > Preventive Medicine > WA 110 Prevention and control of communicable diseases. Transmission of infectious diseases
QV Pharmacology > Drug Standardization. Pharmacognosy. Medicinal Plants > QV 771 Standardization and evaluation of drugs
QW Microbiology and Immunology > Immunotherapy and Hypersensitivity > QW 806 Vaccination
WC Communicable Diseases > Tropical and Parasitic Diseases > WC 750 Malaria
QX Parasitology > Protozoa > QX 135 Plasmodia
QW Microbiology and Immunology > QW 45 Microbial drug resistance. General or not elsewhere classified.
QV Pharmacology > QV 4 General works
QV Pharmacology > QV 38 Drug action.
Faculty: Department: Groups (2002 - 2012) > Molecular & Biochemical Parasitology Group
Digital Object Identifer (DOI): https://doi.org/10.1016/j.bmcl.2008.09.052
Depositing User: Mary Creegan
Date Deposited: 21 Jun 2010 15:21
Last Modified: 06 Feb 2018 13:00
URI: http://archive.lstmed.ac.uk/id/eprint/908

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