Issue 24, 2006
From the journal:

Organic & Biomolecular Chemistry

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

Richard Amewu,a   Andrew V. Stachulski,a   Stephen A. Ward,b   Neil G. Berry,a   Patrick G. Bray,b   Jill Davies,b   Gael Labat,a   Livia Vivasc  and  Paul M. O'Neill*a  

* Corresponding authors

a Department of Chemistry, University of Liverpool, PO Box 147, Liverpool, UK
E-mail: P.M.oneill01@liv.ac.uk
Fax: (+44) 151 794 3588
Tel: (+44) 151 794 3553

b Liverpool School of Tropical Medicine, Pembroke Place, Liverpool, UK

c Department of Infectious and Tropical Diseases, London School of Hygiene and Tropical Medicine, London, UK

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.

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Additions and corrections

Article information

DOI
https://doi.org/10.1039/B613565J
Article type
Communication
Submitted
18 Sep 2006
Accepted
26 Oct 2006
First published
03 Nov 2006

Org. Biomol. Chem., 2006,4, 4431-4436

Permissions

Request permissions

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

R. Amewu, A. V. Stachulski, S. A. Ward, N. G. Berry, P. G. Bray, J. Davies, G. Labat, L. Vivas and P. M. O'Neill, Org. Biomol. Chem., 2006, 4, 4431 DOI: 10.1039/B613565J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements