Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates

Bioorg Med Chem. 2012 Apr 1;20(7):2252-8. doi: 10.1016/j.bmc.2012.02.015. Epub 2012 Feb 13.

Abstract

A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1-5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed by IR, (1)H NMR spectral data and microanalyses. Compounds 1-5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10-100 μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.

MeSH terms

  • Anti-Infective Agents* / chemical synthesis
  • Anti-Infective Agents* / pharmacology
  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Fungi* / drug effects
  • Gram-Negative Bacteria* / drug effects
  • Gram-Positive Bacteria* / drug effects
  • Hep G2 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Organophosphonates* / chemistry
  • Organophosphonates* / pharmacology
  • Phosphorous Acids* / chemistry
  • Phosphorous Acids* / pharmacology
  • Pyridines / chemistry

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Organophosphonates
  • Phosphorous Acids
  • Pyridines
  • phosphonic acid
  • pyridine