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 -