3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: Synthesis using crossed-aldol chemistry and preliminary biological evaluations

Martin G. Banwell; Mark J. Coster; Natasha L. Hungerford; Mary J. Garson; Stephen Su; Andrew C. Kotze; Murray H.G. Munro

doi:10.1039/c1ob06418e

3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: Synthesis using crossed-aldol chemistry and preliminary biological evaluations

Martin G. Banwell^*, Mark J. Coster, Natasha L. Hungerford, Mary J. Garson, Stephen Su, Andrew C. Kotze, Murray H.G. Munro

^*Corresponding author for this work

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10 Citations (Scopus)

Abstract

Compounds 2-5, incorporating various elements of the 3,4′- bis(piperidine) core associated with the sponge-derived alkaloid haliclonacyclamine A (HA, 1), have been prepared through, inter alia, aldol-type reactions of N-substituted piperidin-4-ones and certain derivatives. Screening of these compounds in various assays, including an ecological one, reveals that compound 5 exhibits allelochemical properties similar to those associated with HA itself.

Original language	English
Pages (from-to)	154-161
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	1
DOIs	https://doi.org/10.1039/c1ob06418e
Publication status	Published - 7 Jan 2012

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10.1039/c1ob06418e

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Banwell, M. G., Coster, M. J., Hungerford, N. L., Garson, M. J., Su, S., Kotze, A. C., & Munro, M. H. G. (2012). 3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: Synthesis using crossed-aldol chemistry and preliminary biological evaluations. Organic and Biomolecular Chemistry, 10(1), 154-161. https://doi.org/10.1039/c1ob06418e

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abstract = "Compounds 2-5, incorporating various elements of the 3,4′- bis(piperidine) core associated with the sponge-derived alkaloid haliclonacyclamine A (HA, 1), have been prepared through, inter alia, aldol-type reactions of N-substituted piperidin-4-ones and certain derivatives. Screening of these compounds in various assays, including an ecological one, reveals that compound 5 exhibits allelochemical properties similar to those associated with HA itself.",

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year = "2012",

month = jan,

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doi = "10.1039/c1ob06418e",

language = "English",

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3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: Synthesis using crossed-aldol chemistry and preliminary biological evaluations. / Banwell, Martin G.; Coster, Mark J.; Hungerford, Natasha L. et al.
In: Organic and Biomolecular Chemistry, Vol. 10, No. 1, 07.01.2012, p. 154-161.

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

TY - JOUR

T1 - 3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids

T2 - Synthesis using crossed-aldol chemistry and preliminary biological evaluations

AU - Banwell, Martin G.

AU - Coster, Mark J.

AU - Hungerford, Natasha L.

AU - Garson, Mary J.

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AU - Kotze, Andrew C.

AU - Munro, Murray H.G.

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AB - Compounds 2-5, incorporating various elements of the 3,4′- bis(piperidine) core associated with the sponge-derived alkaloid haliclonacyclamine A (HA, 1), have been prepared through, inter alia, aldol-type reactions of N-substituted piperidin-4-ones and certain derivatives. Screening of these compounds in various assays, including an ecological one, reveals that compound 5 exhibits allelochemical properties similar to those associated with HA itself.

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DO - 10.1039/c1ob06418e

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3,4′-Linked bis(piperidines) related to the haliclonacyclamine class of marine alkaloids: Synthesis using crossed-aldol chemistry and preliminary biological evaluations

Abstract

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