Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines

Bioorg Med Chem Lett. 2008 Feb 15;18(4):1392-6. doi: 10.1016/j.bmcl.2008.01.019. Epub 2008 Jan 11.

Abstract

Diversely substituted 2-pyrrolines have been prepared by a novel multicomponent process involving a reaction of various N-(aryl- and alkylsulfonamido)-acetophenones with aldehydes and malononitrile. While the reaction is highly regioselective, it is not stereoselective, generating a mixture of cis and trans 2-pyrrolines. A number of analogs from both cis and trans 2-pyrroline libraries were found to have antiproliferative activity in human cancer cell lines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetophenones / chemistry
  • Aldehydes / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Growth Processes / drug effects
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Isomerism
  • Jurkat Cells
  • Nitriles / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Acetophenones
  • Aldehydes
  • Antineoplastic Agents
  • Nitriles
  • Pyrroles
  • pyrroline
  • dicyanmethane