The comparative antimalarial properties of weak base and neutral synthetic ozonides

Yuanqing Tang; Sergio Wittlin; Susan A. Charman; Jacques Chollet; Francis C.K. Chiu; Julia Morizzi; Lisa M. Johnson; Josefina Santo Tomas; Christian Scheurer; Chistopher Snyder; Lin Zhou; Yuxiang Dong; William N. Charman; Hugues Matile; Heinrich Urwyler; Arnulf Dorn; Jonathan L. Vennerstrom

doi:10.1016/j.bmcl.2009.11.088

The comparative antimalarial properties of weak base and neutral synthetic ozonides

Yuanqing Tang
, Sergio Wittlin
, Susan A. Charman
, Jacques Chollet
, Francis C.K. Chiu
, Julia Morizzi
, Lisa M. Johnson
, Josefina Santo Tomas
, Christian Scheurer
, Chistopher Snyder
, Lin Zhou
, Yuxiang Dong
, William N. Charman
, Hugues Matile
, Heinrich Urwyler
, Arnulf Dorn
, Jonathan L. Vennerstrom

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

14 Scopus citations

Abstract

Thirty-three N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in Plasmodium berghei-infected mice. A wide range of Log P/D_{pH 7.4} values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.

Original language	English (US)
Pages (from-to)	563-566
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2009.11.088
State	Published - Jan 15 2010
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

1,2,4-Trioxolanes
Antimalarial
Artemisinin
Peroxides
Secondary ozonides

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10.1016/j.bmcl.2009.11.088

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Tang, Y., Wittlin, S., Charman, S. A., Chollet, J., Chiu, F. C. K., Morizzi, J., Johnson, L. M., Tomas, J. S., Scheurer, C., Snyder, C., Zhou, L., Dong, Y., Charman, W. N., Matile, H., Urwyler, H., Dorn, A., & Vennerstrom, J. L. (2010). The comparative antimalarial properties of weak base and neutral synthetic ozonides. Bioorganic and Medicinal Chemistry Letters, 20(2), 563-566. https://doi.org/10.1016/j.bmcl.2009.11.088

Tang, Y, Wittlin, S, Charman, SA, Chollet, J, Chiu, FCK, Morizzi, J, Johnson, LM, Tomas, JS, Scheurer, C, Snyder, C, Zhou, L, Dong, Y, Charman, WN, Matile, H, Urwyler, H, Dorn, A & Vennerstrom, JL 2010, 'The comparative antimalarial properties of weak base and neutral synthetic ozonides', Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 2, pp. 563-566. https://doi.org/10.1016/j.bmcl.2009.11.088

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abstract = "Thirty-three N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in Plasmodium berghei-infected mice. A wide range of Log P/DpH 7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.",

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AU - Chiu, Francis C.K.

AU - Morizzi, Julia

AU - Johnson, Lisa M.

AU - Tomas, Josefina Santo

AU - Scheurer, Christian

AU - Snyder, Chistopher

AU - Zhou, Lin

AU - Dong, Yuxiang

AU - Charman, William N.

AU - Matile, Hugues

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AU - Dorn, Arnulf

AU - Vennerstrom, Jonathan L.

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AB - Thirty-three N-acyl 1,2,4-dispiro trioxolanes (secondary ozonides) were synthesized. For these ozonides, weak base functional groups were not required for high antimalarial potency against Plasmodium falciparum in vitro, but were necessary for high antimalarial efficacy in Plasmodium berghei-infected mice. A wide range of Log P/DpH 7.4 values were tolerated, although more lipophilic ozonides tended to be less metabolically stable.

KW - 1,2,4-Trioxolanes

KW - Antimalarial

KW - Artemisinin

KW - Peroxides

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The comparative antimalarial properties of weak base and neutral synthetic ozonides

Abstract

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