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

Ian T. Crosby; Mark L. Rose; Maree P. Collis; Paula J. de Bruyn; Philip L. C. Keep; Alan D. Robertson

doi:10.1071/CH08177

RESEARCH ARTICLE

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 and Alan D. Robertson ^B ^G

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 61(10) 768-784 https://doi.org/10.1071/CH08177
Submitted: 28 April 2008 Accepted: 15 July 2008 Published: 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.

References

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

Abstract

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