Design, synthesis and biological evaluation of N-arylphenyl-2,2-dichloroacetamide analogues as anti-cancer agents

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7268-71. doi: 10.1016/j.bmcl.2012.07.057. Epub 2012 Jul 23.

Abstract

Our earlier research has shown that N-phenyl-2,2-dichloroacetamide analogues had much higher anti-cancer activity than the lead compound sodium dichloroacetate (DCA). In this current study, a variety of N-arylphenyl-2,2-dichloroacetamide analogues were synthesized via Suzuki coupling reaction and their anti-cancer activity was evaluated. The results showed that N-terphenyl-2,2-dichloroacetamide analogues had satisfactory anti-cancer activity. Among them, N-(3,5-bis(benzo[d][1,3]dioxol-5-yl)phenyl)-2,2-dichloroacetamide (6 k) had an IC(50) of 2.40 μM against KB-3-1 cells, 1.04 μM against H460 cells and 1.73 μM against A549 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemical synthesis*
  • Acetamides / chemistry*
  • Acetamides / toxicity
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Benzodioxoles / chemical synthesis*
  • Benzodioxoles / chemistry
  • Benzodioxoles / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Humans
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Antineoplastic Agents
  • Benzodioxoles
  • N-(3,5-bis(benzo(d)(1,3)dioxol-5-yl)phenyl)-2,2-dichloroacetamide
  • 2,2-dichloroacetamide