Hetero-Diels-Alder approach to Bis(indolyl)methanes

Bioorg Med Chem. 2017 Feb 1;25(3):1122-1131. doi: 10.1016/j.bmc.2016.12.028. Epub 2016 Dec 26.

Abstract

A novel synthetic approach to bis(indolyl)methanes has been established. Our one-pot synthetic strategy based on two consecutive hetero-Diels-Alder cycloaddition reactions of electrophilic conjugated nitrosoalkenes with indoles was extended to a range of new 1-hydroxyiminomethyl-bis(indolyl)methanes. Furthermore, a similar and broad range approach was applied to the synthesis of previously unknown 1-hydrazonomethyl-bis(indolyl)methanes. The biological evaluation of the new bis(indolyl)methanes as anti-cancer agents was investigated.

Keywords: Anti-cancer activity; Azoalkenes; Bis(indolyl)methanes; Hetero-Diels-Alder reaction; Indoles; Leukaemia; Lymphoma; Nitrosoalkenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cycloaddition Reaction
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Methane / pharmacology*
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Indoles
  • Methane