A green approach toward quinoxalines and bis-quinoxalines and their biological evaluation against A431, human skin cancer cell lines

Future Med Chem. 2013 Aug;5(12):1377-90. doi: 10.4155/fmc.13.101.

Abstract

Background: The objective of this study was to develop a practical green procedure to synthesize quinoxalines and bis-quinoxalines and evaluate their inhibitory effects on the viability of A431 human epidermoid carcinoma cells.

Method: A series of quinoxaline and bis-quinoxaline derivatives have been designed and synthesized following a microwave-assisted and bismuth nitrate-catalyzed eco-friendly route. A detailed comparison has been made between microwave-induced protocol with the reactions occurred at room temperature. The structure of the compounds have been elucidated by various spectroscopic methods and finally confirmed by x-ray crystallographic analyses.

Results: Two quinoxaline derivatives, compounds 6 and 12 have demonstrated inhibitory effects on the viability of A431 human epidermoid carcinoma cells when compared with HaCaT nontumorigenic human keratinocyte cells.

Conclusion: Notably, compound 6 inhibits Stat3 phosphorylation/activation in A431 skin cancer cells.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bismuth / chemistry
  • Catalysis
  • Cell Line
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Green Chemistry Technology
  • Humans
  • Microwaves
  • Molecular Conformation
  • Nitrates / chemistry
  • Phosphorylation
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry*
  • Quinoxalines / pharmacology
  • STAT3 Transcription Factor / antagonists & inhibitors
  • STAT3 Transcription Factor / metabolism
  • Skin Neoplasms / metabolism
  • Skin Neoplasms / pathology

Substances

  • Nitrates
  • Quinoxalines
  • STAT3 Transcription Factor
  • bismuth nitrate
  • Bismuth