Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action

Richard K. Haynes; Pai Hendry Hung-On; Arnd Voerste

doi:10.1016/S0040-4039(99)00830-8

Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action

Richard K. Haynes, Pai Hendry Hung-On, Arnd Voerste

Hong Kong University of Science and Technology

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

70 Citations (Scopus)

Abstract

In CH₂Cl₂ in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyartemisinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydroartemisinin. The reactions serve as a model for biological activity in which the act of binding to a protein liberates hydroperoxide.

Original language	English
Pages (from-to)	4715-4718
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(99)00830-8
Publication status	Published - 18 Jun 1999

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10.1016/S0040-4039(99)00830-8

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title = "Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action",

abstract = "In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyartemisinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydroartemisinin. The reactions serve as a model for biological activity in which the act of binding to a protein liberates hydroperoxide.",

author = "Haynes, {Richard K.} and {Hendry Hung-On}, Pai and Arnd Voerste",

note = "Funding Information: Acknowledgments: The Hong Kong Research Grants Council (Grant HKUST 591/95P) and HKUST (RIG.SC03 95196) are thanked for most generous financial support.",

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Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action. / Haynes, Richard K.; Hendry Hung-On, Pai; Voerste, Arnd.
In: Tetrahedron Letters, Vol. 40, No. 25, 18.06.1999, p. 4715-4718.

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

TY - JOUR

T1 - Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action

AU - Haynes, Richard K.

AU - Hendry Hung-On, Pai

AU - Voerste, Arnd

N1 - Funding Information: Acknowledgments: The Hong Kong Research Grants Council (Grant HKUST 591/95P) and HKUST (RIG.SC03 95196) are thanked for most generous financial support.

PY - 1999/6/18

Y1 - 1999/6/18

N2 - In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyartemisinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydroartemisinin. The reactions serve as a model for biological activity in which the act of binding to a protein liberates hydroperoxide.

AB - In CH2Cl2 in the presence of benzylamine, artemisinin transfers an oxygen atom from the intermediate open hydroperoxide to tertiary amines to form N-oxides and N-benzyl-11-azadesoxyartemisinin. Base-catalyzed side reactions interfere with the corresponding reaction involving dihydroartemisinin. The reactions serve as a model for biological activity in which the act of binding to a protein liberates hydroperoxide.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Ring opening of artemisinin (Qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - A chemical model for antimalarial mode of action

Abstract

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