Orally active 1,2,4-trioxanes: synthesis and antimalarial assessment of a new series of 9-functionalized 3-(1-arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against multi-drug-resistant plasmodium yoelii nigeriensis in mice

Journal of Medicinal Chemistry
Chandan SinghSunil Kumar Puri

Abstract

Using easily accessible keto-trioxanes 7a-g as the starting materials, a series of new variously functionalized 1,2,4-trioxanes 10-36 have been prepared and evaluated for antimalarial activity against multi-drug-resistant Plasmodium yoelii nigeriensis in mice in the dose range of 24 mg/kg x 4 days to 96 mg/kg x 4 days by oral route. Trioxanes 10, 12, 14, 16, 18, 20, and 22 have shown promising antimalarial activity. Trioxanes 14 and 18, the two most active compounds of the series, provide 100% and 60% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively. In this model beta-arteether provides 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively.

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Citations

Nov 21, 2012·Journal of Medicinal Chemistry·Chandan SinghRuchir Kant
Nov 7, 2008·Proceedings of the National Academy of Sciences of the United States of America·Frédéric CoslédanBernard Meunier
Nov 17, 2006·Nature Chemical Biology·Adam R Renslo, James H McKerrow
Sep 16, 2008·Bioorganic & Medicinal Chemistry Letters·Chandan SinghSunil K Puri
Oct 19, 2007·Angewandte Chemie·Axel G GriesbeckAngela Raabe
Jan 24, 2014·Beilstein Journal of Organic Chemistry·Alexander O Terent'evValery M Dembitsky
Jan 29, 2021·European Journal of Medicinal Chemistry·Om P S PatelLesetja J Legoabe
Nov 18, 2006·The Journal of Organic Chemistry·Chandan SinghMalvika Sharma
Feb 14, 2013·ACS Medicinal Chemistry Letters·Ranjani MauryaPrem P Yadav
Jul 6, 2010·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Rajendra Pratap SinghShio Kumar Singh

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