ChCl: Gly (DESs) Promote Environmentally Benign Synthesis of Xanthene Derivatives and Their Antitubercular Activity

Molecules. 2021 Jun 16;26(12):3667. doi: 10.3390/molecules26123667.

Abstract

A ChCl: Gly (DESs) promoted environmentally benign method was developed for the first time using the reaction of aryl aldehydes and dimedone to give excellent yields of xanthene analogues. The major application of this present protocol is the use of green solvent, a wide range of substrate, short reaction times, ease of recovery, the recyclability of the catalyst, high reaction yield, and ChCl: Gly as an alternative catalyst and solvent. In addition to this, all the synthesized compounds were evaluated for their in vitro antimycobacterial activity against M. tuberculosis H37Ra (MTB) and M. bovis BCG strains. The compounds 3d, 3e, 3f, and 3j showed significant antitubercular activity against MTB and M. bovis strains with minimum inhibitory concentration (MIC) values of 2.5-15.10 µg/mL and 0.26-14.92 µg/mL, respectively. The compounds 3e, 3f, and 3j were found to be nontoxic against MCF-7, A549, HCT 116, and THP-1 cell lines. All the prepared compounds were confirmed by 1H NMR and 13C NMR analysis.

Keywords: ChCl: Gly; antibacterial activity; antitubercular; cytotoxicity; environmentally benign; xanthenes.

MeSH terms

  • Aldehydes / chemistry
  • Antitubercular Agents / pharmacology
  • Cell Line, Tumor
  • Cyclohexanones / chemistry*
  • Glycerol / chemistry
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Mycobacterium tuberculosis / drug effects
  • Solvents / chemistry*
  • Structure-Activity Relationship
  • Xanthenes / chemical synthesis*
  • Xanthenes / chemistry
  • Xanthenes / isolation & purification

Substances

  • Aldehydes
  • Antitubercular Agents
  • Cyclohexanones
  • Solvents
  • Xanthenes
  • dimedone
  • Glycerol