One-pot four-component domino strategy for the synthesis of novel spirooxindole–pyrrolidine/pyrrolizidine-linked 1,2,3-triazole conjugates via stereo- and regioselective [3+2] cycloaddition reactions: In vitro antibacterial and antifungal studies - 03/01/18

Doi : 10.1016/j.crci.2017.11.009

Randa Sakly ^a, Hayet Edziri ^b, Moheddine Askri ^a,^⁎ , Michael Knorr ^c, Carsten Strohmann ^d, Maha Mastouri ^b
^a Laboratory of Heterocyclic Chemistry Natural Products and Reactivity/CHPNR, Department of Chemistry, Faculty of Science of Monastir, 5000 Monastir, Tunisia
^b Laboratoire des maladies transmissibles et des substances biologiquement actives, Faculté de pharmacie, 5000 Monastir, Tunisia
^c Institut UTINAM ‒ UMR CNRS 6213, Université Bourgogne Franche-Comté, 16, route de Gray, 25030 Besançon, France
^d Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany

^∗Corresponding author.

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abstract

In this study, a series of highly diversified novel functionalized spirooxindolopyrrolidine and spirooxindolopyrrolizidine-linked 1,2,3-triazole conjugates have been synthesized by a one-pot, four-component condensation of (E)-2-(1-propargyl-2-oxoindoline-3-ylidene)acetophenones as bifunctional dipolarophiles, acenaphthenequinone, α-amino acids with substituted aryl azides using coinage metal catalysts. It was found that CuSO₄/Na ascorbate as a catalyst was more performant than Ag₂CO₃ or CuI. The single-crystal X-ray analysis of one of the cycloadducts proves the structure and the regiochemistry of this reaction. The compounds have been screened for their in vitro antibacterial and antifungal activities using the agar dilution method and display good activities.

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Keywords : Spirooxindole, Click chemistry, 1,2,3-Triazoles, Pyrrolidine, Pyrrolizidine