A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity

Stephania Christou; Emel Ozturk; Robin G. Pritchard; Peter Quayle; Ian J. Stratford; Roger C. Whitehead; Katharine F. Williams

doi:10.1016/j.bmcl.2013.07.041

A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity

Stephania Christou, Emel Ozturk, Robin G. Pritchard, Peter Quayle, Ian J. Stratford, Roger C. Whitehead, Katharine F. Williams

Research output: Contribution to journal › Article › peer-review

Abstract

A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported. © 2013 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5066-5069
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2013.07.041
Publication status	Published - 15 Sept 2013

Keywords

Anti-cancer
Natural product
Quinic acid
Synthetic analogue

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2013.07.041

CCDC 859141: Experimental Crystal Structure Determination
Christou, S. (Contributor), Ozturk, E. (Contributor), Pritchard, R. (Contributor), Quayle, P. (Contributor), Stratford, I. (Contributor), Whitehead, R. (Contributor) & Williams, K. F. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccxv07z, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxv07z&sid=DataCite
Dataset
CCDC 872292: Experimental Crystal Structure Determination
Christou, S. (Contributor), Ozturk, E. (Contributor), Pritchard, R. (Contributor), Quayle, P. (Contributor), Stratford, I. (Contributor), Whitehead, R. (Contributor) & Williams, K. F. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccy8pgb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccy8pgb&sid=DataCite
Dataset

Cite this

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title = "A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity",

abstract = "A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported. {\textcopyright} 2013 Elsevier Ltd. All rights reserved.",

keywords = "Anti-cancer, Natural product, Quinic acid, Synthetic analogue",

author = "Stephania Christou and Emel Ozturk and Pritchard, {Robin G.} and Peter Quayle and Stratford, {Ian J.} and Whitehead, {Roger C.} and Williams, {Katharine F.}",

year = "2013",

month = sep,

day = "15",

doi = "10.1016/j.bmcl.2013.07.041",

language = "English",

volume = "23",

pages = "5066--5069",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "1464-3405",

publisher = "Elsevier BV",

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TY - JOUR

T1 - A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity

AU - Christou, Stephania

AU - Ozturk, Emel

AU - Pritchard, Robin G.

AU - Quayle, Peter

AU - Stratford, Ian J.

AU - Whitehead, Roger C.

AU - Williams, Katharine F.

PY - 2013/9/15

Y1 - 2013/9/15

N2 - A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported. © 2013 Elsevier Ltd. All rights reserved.

AB - A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported. © 2013 Elsevier Ltd. All rights reserved.

KW - Anti-cancer

KW - Natural product

KW - Quinic acid

KW - Synthetic analogue

U2 - 10.1016/j.bmcl.2013.07.041

DO - 10.1016/j.bmcl.2013.07.041

M3 - Article

SN - 1464-3405

VL - 23

SP - 5066

EP - 5069

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 18

ER -

A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity

Abstract

Keywords

UN SDGs

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Datasets

CCDC 859141: Experimental Crystal Structure Determination

CCDC 872292: Experimental Crystal Structure Determination

Cite this