Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone

Article

<< Previous

Next >>

Contents Vol 61(10)

doi:10.1071/CH08177

Antiviral Agents. I. Synthesis and Antiviral Evaluation of Trimeric Naphthoquinone Analogues of Conocurvone

Ian T. Crosby ^A ^H, Mark L. Rose ^A ^C, Maree P. Collis ^B ^D, Paula J. de Bruyn ^A ^E, Philip L. C. Keep ^B ^F, Alan D. Robertson ^B ^G

^A Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University (Parkville Campus), 381 Royal Parade, Parkville, VIC 3052, Australia.
^B AMRAD Operations Pty Ltd, 576 Swan Street, Richmond, VIC 3121, Australia.
^C Present address: PROBE Analytical, 1/19-23 Paramount Road, West Footscray, VIC 3012, Australia.
^D Present address: Lethbridge Wines, 74 Burrows Road, Lethbridge, VIC 3332, Australia.
^E Present address: DaviesCollisonCave, 1 Nicholson Street, Melbourne, VIC 3000, Australia.
^F Present address: CSL, 45 Poplar Road, Parkville, VIC 3052, Australia.
^G Present address: Pharmaxis Ltd, 2/10 Rodborough Road, Frenchs Forest, NSW 2086, Australia.
^H Corresponding author. Email: ian.crosby@vcp.monash.edu.au





	PDF (571 KB) $25



	Export Citation

Print

Australian Journal of Chemistry 61(10) 768–784 http://dx.doi.org/10.1071/CH08177
Submitted: 28 April 2008 Accepted: 15 July 2008 Published online: 6 October 2008

Abstract

Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity.