Anti-Plasmodium activity of imidazolium and triazolium salts

Bioorganic & Medicinal Chemistry
Jason Z VlahakisWalter A Szarek

Abstract

We have previously reported that tetrazolium salts were both potent and specific inhibitors of Plasmodium replication, and that they appear to interact with a parasite component that is both essential and conserved. The use of tetrazolium salts in vivo is limited by the potential reduction of the tetrazolium ring to form an inactive, neutral acyclic formazan. To address this issue imidazolium and triazolium salts were synthesized and evaluated as Plasmodium inhibitors. Many of the imidazolium and triazolium salts were highly potent with active concentrations in the nanomolar range in Plasmodium falciparum cultures, and specific to Plasmodium with highly favorable therapeutic ratios. The results corroborate our hypothesis that an electron-deficient core is required so that the compound may thereby interact with a negatively charged moiety on the parasite merozoite; the side groups in the compound then form favorable interactions with adjacent parasite components and thereby determine both the potency and selectivity of the compound.

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Citations

Feb 5, 2013·Bioorganic & Medicinal Chemistry·Yin GaoInka Brockhausen
Jul 9, 2013·European Journal of Medicinal Chemistry·Lan-Xiang LiuXiao-Dong Yang
Feb 16, 2013·The Journal of Organic Chemistry·Dong TangBao-Hua Chen
Dec 24, 2013·International Journal of Antimicrobial Agents·Paula Faral-TelloCarlos Robello
Jun 21, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jingwei LiangFanhao Meng
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Jan 17, 2019·Chemistry : a European Journal·Felix SchroeterThomas Strassner
Aug 28, 2013·Chemical Society Reviews·Siti Nurhanna Riduan, Yugen Zhang
Jun 18, 2021·Organic Letters·Marcin BudnyAndrzej Wolan

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