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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| Published in | Organometallics Vol. 32; no. 20; pp. 5713 - 5719 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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28.10.2013
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| Abstract | 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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| AbstractList | 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. 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-S 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. |
| Author | Kumar, Kewal Carrère-Kremer, Séverine Biot, Christophe Kumar, Vipan Guérardel, Yann Kremer, Laurent |
| AuthorAffiliation | DIMNP Université Montpellier 2I CNRS Université Lille 1 Guru Nanak Dev University |
| AuthorAffiliation_xml | – name: DIMNP – name: Université Montpellier 2I – name: Guru Nanak Dev University – name: Université Lille 1 – name: CNRS |
| Author_xml | – sequence: 1 givenname: Kewal surname: Kumar fullname: Kumar, Kewal – sequence: 2 givenname: Séverine surname: Carrère-Kremer fullname: Carrère-Kremer, Séverine – sequence: 3 givenname: Laurent surname: Kremer fullname: Kremer, Laurent – sequence: 4 givenname: Yann surname: Guérardel fullname: Guérardel, Yann – sequence: 5 givenname: Christophe surname: Biot fullname: Biot, Christophe email: christophe.biot@univ-lille1.fr, vipan_org@yahoo.com – sequence: 6 givenname: Vipan surname: Kumar fullname: Kumar, Vipan email: christophe.biot@univ-lille1.fr, vipan_org@yahoo.com |
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| Keywords | ORGANOMETALLIC COMPOUNDS DESIGN CYCLOADDITION EN-ROUTE CHALCONE DERIVATIVES ANTICANCER ANALOGS TUBERCULOSIS BIOLOGICAL EVALUATION AGENTS BETA-LACTAM-FERROCENE |
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| Snippet | A Cu-mediated azide–alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure–activity... A Cu-mediated azide-alkyne cycloaddition protocol has been employed for the synthesis of 16 different triazoles to probe the antitubercular structure activity... |
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| SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Physical Sciences Science & Technology |
| Title | 1H‑1,2,3-Triazole-Tethered Isatin–Ferrocene and Isatin–Ferrocenylchalcone Conjugates: Synthesis and in Vitro Antitubercular Evaluation |
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