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Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors. / Florence, Gordon J.; Fraser, Andrew L.; Gould, Eoin R. et al.
In: ChemMedChem, Vol. 9, No. 11, 01.11.2014, p. 2548-2556.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Florence, GJ, Fraser, AL, Gould, ER, King, EFB, Menzies, SK, Morris, JC, Tulloch, LB & Smith, TK 2014, 'Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors', ChemMedChem, vol. 9, no. 11, pp. 2548-2556. https://doi.org/10.1002/cmdc.201402272

APA

Florence, G. J., Fraser, A. L., Gould, E. R., King, E. F. B., Menzies, S. K., Morris, J. C., Tulloch, L. B., & Smith, T. K. (2014). Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors. ChemMedChem, 9(11), 2548-2556. https://doi.org/10.1002/cmdc.201402272

Vancouver

Florence GJ, Fraser AL, Gould ER, King EFB, Menzies SK, Morris JC et al. Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors. ChemMedChem. 2014 Nov 1;9(11):2548-2556. doi: 10.1002/cmdc.201402272

Author

Florence, Gordon J. ; Fraser, Andrew L. ; Gould, Eoin R. et al. / Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors. In: ChemMedChem. 2014 ; Vol. 9, No. 11. pp. 2548-2556.

Bibtex

@article{407064c1e0fa4ec7b3db6ba82a10169a,
title = "Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors",
abstract = "Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are detailed. The analogues synthesized display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness, also known as Human African Trypanosomiasis (HAT). A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4-triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure-activity relationship studies. Together, the biological potency and calculated lipophilicity values indicate that while there is room for improvement, these derivatives may represent a promising novel class of anti-HAT agents.",
keywords = "acetogenin, Human African Trypanosomiasis (HAT), natural product analogues, neglected diseases, stereochemistry, Trypanosoma brucei",
author = "Florence, {Gordon J.} and Fraser, {Andrew L.} and Gould, {Eoin R.} and King, {Elizabeth F.B.} and Menzies, {Stefanie K.} and Morris, {Joanne C.} and Tulloch, {Lindsay B.} and Smith, {Terry K.}",
year = "2014",
month = nov,
day = "1",
doi = "10.1002/cmdc.201402272",
language = "English",
volume = "9",
pages = "2548--2556",
journal = "ChemMedChem",
issn = "1860-7179",
publisher = "John Wiley and Sons Ltd",
number = "11",

}

RIS

TY - JOUR

T1 - Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors

AU - Florence, Gordon J.

AU - Fraser, Andrew L.

AU - Gould, Eoin R.

AU - King, Elizabeth F.B.

AU - Menzies, Stefanie K.

AU - Morris, Joanne C.

AU - Tulloch, Lindsay B.

AU - Smith, Terry K.

PY - 2014/11/1

Y1 - 2014/11/1

N2 - Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are detailed. The analogues synthesized display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness, also known as Human African Trypanosomiasis (HAT). A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4-triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure-activity relationship studies. Together, the biological potency and calculated lipophilicity values indicate that while there is room for improvement, these derivatives may represent a promising novel class of anti-HAT agents.

AB - Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are detailed. The analogues synthesized display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness, also known as Human African Trypanosomiasis (HAT). A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4-triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure-activity relationship studies. Together, the biological potency and calculated lipophilicity values indicate that while there is room for improvement, these derivatives may represent a promising novel class of anti-HAT agents.

KW - acetogenin

KW - Human African Trypanosomiasis (HAT)

KW - natural product analogues

KW - neglected diseases

KW - stereochemistry

KW - Trypanosoma brucei

U2 - 10.1002/cmdc.201402272

DO - 10.1002/cmdc.201402272

M3 - Journal article

C2 - 25145275

AN - SCOPUS:84927128266

VL - 9

SP - 2548

EP - 2556

JO - ChemMedChem

JF - ChemMedChem

SN - 1860-7179

IS - 11

ER -