The comparative antimalarial properties of weak base and neutral synthetic ozonides

Yuanqing Tang; Sergio Wittlin; Susan Ann Charman; Jacques Chollet; Francis Chi Keung Chiu; Julia Morizzi; Lisa Johnson; Josefina Santo Tomas; Christian Scheurer; Christopher Snyder; Lin Zhou; Yuxiang Dong; William Neil Charman; Hugues Matile; Heinrich Urwyler; Arnulf Dorn; Jonathan 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 Ann Charman, Jacques Chollet, Francis Chi Keung Chiu, Julia Morizzi, Lisa Johnson, Josefina Santo Tomas, Christian Scheurer, Christopher Snyder, Lin Zhou, Yuxiang Dong, William Neil Charman, Hugues Matile, Heinrich Urwyler, Arnulf Dorn, Jonathan Vennerstrom

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

14 Citations (Scopus)

Abstract

Thirty-three N-acyl 1,2,4-dispiro tioxolanes (secondary ozonides) were synthesised. For these ozonides, weak base function 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 ph7.4 values were tolerated, although more liophilic ozonides tended to be less metabolically stable.

Original language	English
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
Publication status	Published - 2010

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10.1016/j.bmcl.2009.11.088

Cite this

Tang, Y., Wittlin, S., Charman, S. A., Chollet, J., Chiu, F. C. K., Morizzi, J., Johnson, L., Santo Tomas, J., Scheurer, C., Snyder, C., Zhou, L., Dong, Y., Charman, W. N., Matile, H., Urwyler, H., Dorn, A., & Vennerstrom, J. (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

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abstract = "Thirty-three N-acyl 1,2,4-dispiro tioxolanes (secondary ozonides) were synthesised. For these ozonides, weak base function 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 ph7.4 values were tolerated, although more liophilic ozonides tended to be less metabolically stable.",

author = "Yuanqing Tang and Sergio Wittlin and Charman, {Susan Ann} and Jacques Chollet and Chiu, {Francis Chi Keung} and Julia Morizzi and Lisa Johnson and {Santo Tomas}, Josefina and Christian Scheurer and Christopher Snyder and Lin Zhou and Yuxiang Dong and Charman, {William Neil} and Hugues Matile and Heinrich Urwyler and Arnulf Dorn and Jonathan Vennerstrom",

year = "2010",

doi = "10.1016/j.bmcl.2009.11.088",

language = "English",

volume = "20",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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Tang, Y, Wittlin, S, Charman, SA, Chollet, J, Chiu, FCK, Morizzi, J, Johnson, L, Santo Tomas, J, Scheurer, C, Snyder, C, Zhou, L, Dong, Y, Charman, WN, Matile, H, Urwyler, H, Dorn, A & Vennerstrom, J 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

TY - JOUR

T1 - The comparative antimalarial properties of weak base and neutral synthetic ozonides

AU - Tang, Yuanqing

AU - Wittlin, Sergio

AU - Charman, Susan Ann

AU - Chollet, Jacques

AU - Chiu, Francis Chi Keung

AU - Morizzi, Julia

AU - Johnson, Lisa

AU - Santo Tomas, Josefina

AU - Scheurer, Christian

AU - Snyder, Christopher

AU - Zhou, Lin

AU - Dong, Yuxiang

AU - Charman, William Neil

AU - Matile, Hugues

AU - Urwyler, Heinrich

AU - Dorn, Arnulf

AU - Vennerstrom, Jonathan

PY - 2010

Y1 - 2010

N2 - Thirty-three N-acyl 1,2,4-dispiro tioxolanes (secondary ozonides) were synthesised. For these ozonides, weak base function 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 ph7.4 values were tolerated, although more liophilic ozonides tended to be less metabolically stable.

AB - Thirty-three N-acyl 1,2,4-dispiro tioxolanes (secondary ozonides) were synthesised. For these ozonides, weak base function 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 ph7.4 values were tolerated, although more liophilic ozonides tended to be less metabolically stable.

U2 - 10.1016/j.bmcl.2009.11.088

DO - 10.1016/j.bmcl.2009.11.088

M3 - Article

SN - 0960-894X

VL - 20

SP - 563

EP - 566

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 2

ER -