Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2527-32. doi: 10.1016/j.bmcl.2011.02.039. Epub 2011 Feb 15.

Abstract

Ionic liquid ethyl ammonium nitrate is used as an excellent catalyst and solvent for three-component one-pot reaction of an aldehydes, amines and diethylphosphite to form novel α-aminophosphonates at room temperature. Among the various catalysts, the preparation of ethyl ammonium nitrate is an environmental friendly, cost effective and recyclable catalyst. Compounds 4b, 4c, 4d, 4f and 4j were found more potent antibacterials against pathogenic microorganisms. Whereas, compounds 4a, 4g, 4h and 4j inhibits growth of active Escherichia coli NCIM 2645 and Salmonella typhi NCIM 2501. Compound 4j was found a promising antiproliferative agent against A549 and SK-MEL2 human melanoma cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / toxicity
  • Catalysis
  • Cell Line, Tumor
  • Humans
  • Ionic Liquids / chemistry*
  • Microbial Sensitivity Tests
  • Nitrates / chemistry
  • Organophosphonates / chemical synthesis
  • Organophosphonates / chemistry*
  • Organophosphonates / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Ionic Liquids
  • Nitrates
  • Organophosphonates
  • ammonium nitrate