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    Novel nitro(triazole/imidazole)-based heteroarylamides/sulfonamides as potential antitrypanosomal agents 
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    • Novel nitro(triazole/imidazole)-based heteroarylamides/sulfonamides as potential antitrypanosomal agents
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    • Novel nitro(triazole/imidazole)-based heteroarylamides/sulfonamides as potential antitrypanosomal agents
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    Novel nitro(triazole/imidazole)-based heteroarylamides/sulfonamides as potential antitrypanosomal agents

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    Published version
    Embargoed until: 5555-01-01
    Volume
    87
    Pagination
    79 - 88 (9)
    Publisher URL
    http://www.sciencedirect.com/science/article/pii/S0223523414008630
    DOI
    10.1016/j.ejmech.2014.09.045
    Journal
    European Journal of Medicinal Chemistry
    Metadata
    Show full item record
    Abstract
    We have previously shown that 3-nitro-1H-1,2,4-triazole-based arylamides and arylsulfonamides demonstrate significant activity in vitro against Trypanosoma cruzi, the causative parasite of Chagas disease. More importantly, several such analogs displayed significant antichagasic activity in vivo, superior to that of benznidazole, the current clinical standard. We now report the synthesis and in vitro evaluation of a small series of novel nitro(triazole/imidazole)-based heteroarylamides/sulfonamides (including 3-nitrotriazole-, 2- and 4-nitroimidazole-based compounds) as potential antitrypanosomal agents. All nitrotriazoles displayed significant growth inhibitory properties against T. cruzi with the most potent generating IC50 values of <1 mM and up to >1400-fold selectivity toward the parasite. The 2-nitroimidazole-based derivatives were moderately active against T. cruzi and displayed selectivity <50, while the 4-nitroimidazoles were mostly inactive. Several 3-nitrotriazole-based analogs showed activity against Trypanosoma brucei rhodesiense but none of the tested compounds displayed activity toward Leishmania donovani. From the detailed SARs presented here, we identified the 3-nitrotriazole-based chlorinated thiophene/benzothiophene sulfonamides/amides as being the most active antichagasic compounds, displaying up to 14-fold higher potency against T. cruzi than the reference compound benznidazole.
    Authors
    Papadopoulou, MV; Bloomer, WD; Rosenzweig, HS; WILKINSON, SR; Kaiser, M
    URI
    http://qmro.qmul.ac.uk/xmlui/handle/123456789/10880
    Collections
    • Chemistry and Biochemistry [209]
    Language
    English
    Licence information
    doi:10.1016/j.ejmech.2014.09.045
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