The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity

Paul M. O' Neill; Laurence P. Bishop; Natalie L. Searle; James L. Maggs; Steve Ward; Patrick G. Bray; Richard C. Storr; B. Kevin Park

doi:10.1016/s0040-4039(97)00874-5

The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity

Paul M. O' Neill, Laurence P. Bishop, Natalie L. Searle, James L. Maggs, Steve Ward, Patrick G. Bray, Richard C. Storr, B. Kevin Park

University of Liverpool

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

47 Citations (Scopus)

Abstract

Arlenene 4 reacts with FeCl2.4H20 in acetonitrile or with hemin / N-acetylcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with Zn/AcOH, a model of NADH dehydrogenase, results in the formation of the diol 5 in 80% yield The formation of the enone 6 indicates that arteflene fragments to a non-stabilised carbon-centred radical. This radical intermediate is proposed to mediate the potent antimalarial activity of 4.

Original language	English
Pages (from-to)	4263-4266
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	24
DOIs	https://doi.org/10.1016/s0040-4039(97)00874-5
Publication status	Published - 16 Jun 1997
Externally published	Yes

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O' Neill, P. M., Bishop, L. P., Searle, N. L., Maggs, J. L., Ward, S., Bray, P. G., Storr, R. C., & Park, B. K. (1997). The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity. Tetrahedron Letters, 38(24), 4263-4266. https://doi.org/10.1016/s0040-4039(97)00874-5

@article{ada07f212e68470786eba4be0ceb3a4b,

title = "The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity",

abstract = "Arlenene 4 reacts with FeCl2.4H20 in acetonitrile or with hemin / N-acetylcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with Zn/AcOH, a model of NADH dehydrogenase, results in the formation of the diol 5 in 80\% yield The formation of the enone 6 indicates that arteflene fragments to a non-stabilised carbon-centred radical. This radical intermediate is proposed to mediate the potent antimalarial activity of 4.",

author = "\{O' Neill\}, \{Paul M.\} and Bishop, \{Laurence P.\} and Searle, \{Natalie L.\} and Maggs, \{James L.\} and Steve Ward and Bray, \{Patrick G.\} and Storr, \{Richard C.\} and Park, \{B. Kevin\}",

year = "1997",

month = jun,

day = "16",

doi = "10.1016/s0040-4039(97)00874-5",

language = "English",

volume = "38",

pages = "4263--4266",

journal = "Tetrahedron Letters",

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O' Neill, PM, Bishop, LP, Searle, NL, Maggs, JL, Ward, S, Bray, PG, Storr, RC & Park, BK 1997, 'The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity', Tetrahedron Letters, vol. 38, no. 24, pp. 4263-4266. https://doi.org/10.1016/s0040-4039(97)00874-5

The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity. / O' Neill, Paul M.; Bishop, Laurence P.; Searle, Natalie L. et al.
In: Tetrahedron Letters, Vol. 38, No. 24, 16.06.1997, p. 4263-4266.

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

TY - JOUR

T1 - The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity: Implications for the mechanism of antimalarial activity

AU - O' Neill, Paul M.

AU - Bishop, Laurence P.

AU - Searle, Natalie L.

AU - Maggs, James L.

AU - Ward, Steve

AU - Bray, Patrick G.

AU - Storr, Richard C.

AU - Park, B. Kevin

PY - 1997/6/16

Y1 - 1997/6/16

N2 - Arlenene 4 reacts with FeCl2.4H20 in acetonitrile or with hemin / N-acetylcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with Zn/AcOH, a model of NADH dehydrogenase, results in the formation of the diol 5 in 80% yield The formation of the enone 6 indicates that arteflene fragments to a non-stabilised carbon-centred radical. This radical intermediate is proposed to mediate the potent antimalarial activity of 4.

AB - Arlenene 4 reacts with FeCl2.4H20 in acetonitrile or with hemin / N-acetylcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with Zn/AcOH, a model of NADH dehydrogenase, results in the formation of the diol 5 in 80% yield The formation of the enone 6 indicates that arteflene fragments to a non-stabilised carbon-centred radical. This radical intermediate is proposed to mediate the potent antimalarial activity of 4.

U2 - 10.1016/s0040-4039(97)00874-5

DO - 10.1016/s0040-4039(97)00874-5

M3 - Article

SN - 0040-4039

VL - 38

SP - 4263

EP - 4266

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -