Synthesis of mono- and di-substituted 2,4,5-trifluorobenzoic acid synthons, key precursors for biologically active 6-fluoroquinolones |
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Authors: | Guillaume Anquetin |
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Affiliation: | Laboratoire de Chimie Bioorganique UMR-CNRS 6001, Université de Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France |
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Abstract: | In the search for new potent antiparasitical fluoroquinolones, a QSAR analysis by molecular connectivity led to the design of R5 (Me or Et)/R8 (MeO, Me or Et)-substituted analogs of the most powerful antibacterial or antiparasitical fluoroquinolones known so far. Unfortunately, the synthetic schemes that were elaborated in literature for 3- and 3,6-di-substituted 2,4,5-trifluorobenzoic acids, the key precursors of the target R5/R8-substituted 6-fluoroquinolones, led in our hands to poor yields and/or to inextricable mixtures of derivatives. This led us to reinvestigate the key alkylation steps of the 2,4,5-trifluorophenyl-oxazoline synthons and the subsequent deprotection of their oxazoline into acid with the aim of optimising the syntheses of 3- and 3,6-di-substituted 2,4,5-trifluorobenzoic acids, which constitute the entries to our target derivatives. |
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Keywords: | Fluoroquinolone Antiparasitical Plasmodium Toxoplasma gondii |
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