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

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 a...

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Bibliographic Details
Published inOrganometallics Vol. 32; no. 20; pp. 5713 - 5719
Main Authors Kumar, Kewal, Carrère-Kremer, Séverine, Kremer, Laurent, Guérardel, Yann, Biot, Christophe, Kumar, Vipan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOMETALLIC COMPOUNDS
DESIGN
CYCLOADDITION EN-ROUTE
CHALCONE DERIVATIVES
ANTICANCER
ANALOGS
TUBERCULOSIS
BIOLOGICAL EVALUATION
AGENTS
BETA-LACTAM-FERROCENE
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Summary: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.
ISSN:0276-7333
1520-6041
DOI:10.1021/om301157z