Design and synthesis of screening libraries based on the muurolane natural product scaffold

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Title Design and synthesis of screening libraries based on the muurolane natural product scaffold
Author Barnes, Emma Catherine; Choomuenwai, Vanida; Andrews, Katherine Thea; Quinn, Ronald J; Davis, Rohan Andrew
Journal Name Organic & Biomolecular Chemistry
Year Published 2012
Place of publication United Kingdom
Publisher RSC Publishing
Abstract The plant-derived natural product 14-hydroxy-6,12-muuroloadien-15-oic acid (1) was identified as a unique scaffold that could be chemically elaborated to generate novel lead- or drug-like screening libraries. Prior to synthesis a virtual library was generated and prioritised based on drug-like physicochemical parameters such as log P, log D5.5, hydrogen bond donors/acceptors, and molecular weight. The natural product scaffold (1) was isolated from the endemic Australian plant Eremophila mitchellii and then utilised in the parallel solution-phase generation of two series of analogues. The first library consisted of six semi-synthetic amide derivatives, whilst the second contained six carbamate analogues. These libraries have been evaluated for antimalarial activity using a chloroquine-sensitive Plasmodium falciparum line (3D7) and several compounds displayed low to moderate activity with IC50 values ranging from 14 to 33 μM.
Peer Reviewed Yes
Published Yes
Alternative URI http://dx.doi.org/10.1039/c2ob00029f
Volume 10
Issue Number 20
Page from 4015
Page to 4023
ISSN 1477-0539
Date Accessioned 2012-07-12
Date Available 2013-06-07T04:37:27Z
Language en_US
Research Centre Eskitis Institute for Drug Discovery
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Biologically Active Molecules
URI http://hdl.handle.net/10072/48207
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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