Rapid access to α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile and the anti-proliferative activities of the products

Org Biomol Chem. 2014 Jan 14;12(2):355-61. doi: 10.1039/c3ob41921e.

Abstract

An effective and convenient method has been developed for the preparation of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile in the presence of zinc dust, acetic acid and triethylamine. This protocol presents a simple, rapid and pot/step economical strategy for preparing biologically interesting α-carbolines with moderate anti-tumor activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemistry*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carbolines / chemical synthesis
  • Carbolines / chemistry
  • Carbolines / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Ketones / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Acetonitriles
  • Antineoplastic Agents
  • Carbolines
  • Ketones
  • alpha-carboline