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1H-1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation

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Department of Chemistry, Guru Nanak Dev University, Amritsar-143005, Punjab, India
Laboratoire de Dynamique des Interactions Membranaires Normales et Pathologiques, UMR 5235 CNRS, Université Montpellier 2I, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France
§ INSERM, DIMNP, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France
Unité de Glycobiologie Structurale et Fonctionnelle, Université Lille 1, F-59650 Villeneuve d’Ascq, France
# CNRS, UMR 8576, F-59650 Villeneuve d’Ascq, France
Cite this: Organometallics 2013, 32, 20, 5713–5719
Publication Date (Web):March 21, 2013
Copyright © 2013 American Chemical Society

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    Abstract Image

    A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity relationships within the isatin–ferrocene–triazole conjugate family. The antitubercular evaluation studies revealed a marked improvement in activity with the introduction of ferrocene nucleus among precursors N-alkylazido isatins with a prefernce for halogen (F, Cl) substituent at C-5 position of isatin as well as propyl chain length as a spacer. The induction of a chalcone nucleus resulted in the enhanced antimycobacterial efficacy irrespective of the subtituent and alkyl chain length as evidenced by the isatin–ferrocenylchalcone hybrids. The described protocol is the first successful attempt of the amalgamation of ferrocene–isatin nuclei tethered via a triazole linker.

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    Structures and scanned (1H, 13C) NMR spectra for the compounds viz. 3c, 3f, 3g, 8a, 8f, 8g, 8h. This material is available free of charge via the Internet at

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