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Issue 5, 2013
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Azide–alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered β-lactam–ferrocene and β-lactam–ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation

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Abstract

A diverse range of triazoles were prepared following well established, Cu-mediated azidealkyne cycloaddition reactions with the aim of probing the anti-tubercular structure–activity relationships (SAR) within the β-lactam–ferrocene–triazole conjugate family. The anti-tubercular evaluation studies of the synthesized conjugates revealed that none of the scaffolds exhibited any activity that restricted mycobacterial growth even at high doses. The introduction of various substituents onto the N-1 of the β-lactam ring, introducing mono- or di-ferrocenylchalcone substituents at the C-3 position as well as introducing a spacer of varying chain length failed to produce any significant enhancement in the activity profiles. The described protocol was a successful attempt on the inclusion of a ferrocene nucleus in the β-lactam family tethered via triazole linkers having metabolic stability and physicochemical favourability.

Graphical abstract: Azide–alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered β-lactam–ferrocene and β-lactam–ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation

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Publication details

The article was received on 17 Sep 2012, accepted on 09 Oct 2012 and first published on 10 Oct 2012


Article type: Paper
DOI: 10.1039/C2DT32148C
Citation: Dalton Trans., 2013,42, 1492-1500
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    Azide–alkyne cycloaddition en route towards 1H-1,2,3-triazole-tethered β-lactam–ferrocene and β-lactam–ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation

    K. Kumar, S. Carrère-Kremer, L. Kremer, Y. Guérardel, C. Biot and V. Kumar, Dalton Trans., 2013, 42, 1492
    DOI: 10.1039/C2DT32148C

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