Azide-alkyne cycloaddition en route to 4-aminoquinoline-ferrocenylchalcone conjugates: synthesis and anti-TB evaluation

Future Med Chem. 2017 Oct;9(15):1701-1708. doi: 10.4155/fmc-2017-0098. Epub 2017 Sep 4.

Abstract

Aim: Tuberculosis is responsible for 9.6 million infections and 1.5 million deaths in 2015. The development of multidrug-resistant and extensively drug-resistant strains has impeded the development of effective antitubercular therapy. Results/methodology: The present manuscript describes the synthesis of a series of 4-aminoquinoline-ferrocenylchalcone conjugates via Cu-promoted Huisgen's azide-alkyne cycloaddition reaction and evaluation of their antitubercular activities against mc26230 strain of Mycobacterium tuberculosis. The conjugate 11j proved to be the most potent of the synthesized conjugates with a minimum inhibitory concentration (MIC99) value of 30 μM and proved to be noncytotoxic against HeLa cells.

Conclusion: The synthesized conjugates can act as starting point for the development of new antitubercular agents. Synthesis and antitubercular evaluation of 1H-1,2,3-triazole-tethered 4-aminoquinoline-ferrocenylchalcone conjugates. [Formula: see text].

Keywords: 4-aminoquinoline; antitubercular activity; ferrocenyl chalcone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Aminoquinolines / chemistry*
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / pharmacology*
  • Azides / chemistry
  • Cell Survival / drug effects
  • Chalcone / chemical synthesis*
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Cycloaddition Reaction*
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects

Substances

  • Alkynes
  • Aminoquinolines
  • Antitubercular Agents
  • Azides
  • Chalcone
  • 4-aminoquinoline