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
Volume 10
Issue Number 20
Page from 4015
Page to 4023
ISSN 1477-0539
Date Accessioned 2012-07-12
Language en_US
Research Centre Eskitis Institute for Drug Discovery
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Biologically Active Molecules
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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