The synthesis and biological evaluation of some caffeic acid amide derivatives: E-2-cyano-(3-substituted phenyl)acrylamides

Bioorg Med Chem Lett. 2009 Apr 1;19(7):1861-5. doi: 10.1016/j.bmcl.2009.02.081. Epub 2009 Feb 25.

Abstract

A series of caffeic acid amide derivatives 2-cyano-(3-substituted phenyl)acrylamides were synthesized via Knoevenogal condensation of substituted benzaldehydes with cyanoacetamides. The structure of compound 1f was determined as E-isomer by X-ray diffractive analysis. The biological screening tests in vitro showed that compound 1b has obvious inhibitory activities against human gastric carcinoma cell line BGC-823, human nasopharyngeal carcinoma cell line KB and human hepatoma cell line BEL-7402 with IC(50) values of 5.6 microg/mL, 13.1 microg/mL and 12.5 microg/mL, respectively. Some preliminary structure-activity relationships (SAR) were also proposed which may provide a direction for further study.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylamides / chemical synthesis*
  • Acrylamides / chemistry
  • Acrylamides / pharmacology*
  • Caffeic Acids / chemistry*
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Humans
  • Inhibitory Concentration 50
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Acrylamides
  • Caffeic Acids
  • Nitriles