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Synthesis and evaluation of original bioisosteres of bacterial type IIA topoisomerases inhibitors

Abstract : A recently discovered series of inhibitors of the ATPase function of bacterial type IIA topoisomerases featuring a carboxypyrrole component led us to attempt to replace this group with a potentially bioisosteric carboxypyrazole. Accordingly, synthetic pathways to 2-(4-(1H-pyrazole-5-carboxamido)piperidin-1-yl)thiazole-5-carboxylic acids or 2-(4-(N-methyl-1H-pyrazole- 5-carboxamido)piperidin-1-yl)thiazole-5-carboxylic acids featuring an array of substituents on the pyrazole ring were explored. Unfortunately, none of the analogues made were effective on the ATPase function of Mycobacterium tuberculosis gyrase as well on the DNA supercoiling activity of the whole gyrase of M. tuberculosis and Escherichia coli. However, this work is still providing original insights in chemistry as well as in the structure–activity relationships of this series of inhibitors
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Submitted on : Monday, October 24, 2016 - 11:56:54 AM
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Stéphanie Petrella, Alexandra Aubry, Geneviève Janvier, Eloi P. Coutant, Alex Cartier, et al.. Synthesis and evaluation of original bioisosteres of bacterial type IIA topoisomerases inhibitors. Canadian Journal of Chemistry, 2016, 94 (3), pp.240-250. ⟨10.1139/cjc-2015-0475⟩. ⟨pasteur-01386561⟩



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