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Issue 20, 2012
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Design and synthesis of screening libraries based on the muurolane natural product scaffold

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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.

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

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Publication details

The article was received on 05 Jan 2012, accepted on 20 Feb 2012 and first published on 15 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB00029F
Citation: Org. Biomol. Chem., 2012,10, 4015-4023
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    Design and synthesis of screening libraries based on the muurolane natural product scaffold

    E. C. Barnes, V. Choomuenwai, K. T. Andrews, R. J. Quinn and R. A. Davis, Org. Biomol. Chem., 2012, 10, 4015
    DOI: 10.1039/C2OB00029F

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