Novel approach to bis(indolyl)methanes: de novo synthesis of 1-hydroxyiminomethyl derivatives with anti-cancer properties

Eur J Med Chem. 2015 Mar 26;93:9-15. doi: 10.1016/j.ejmech.2015.01.050. Epub 2015 Jan 26.

Abstract

A versatile and broad range approach to previously unknown bis(indolyl)methane oximes based on two consecutive hetero Diels-Alder cycloaddition reactions of electrophilic conjugated nitrosoalkenes with indoles is disclosed. The cytotoxic properties and selectivity of some adducts against several human cancer cell lines pointing to a promising role in the development of anti-tumoural drugs, in particular for leukaemia and lymphoma.

Keywords: Anti-cancer activity; Bis(indolyl)methanes; Indoles; Leukaemia; Lymphoma; Nitrosoalkenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / adverse effects
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Culture Techniques
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cycloaddition Reaction
  • Drug Design*
  • Humans
  • Indoles / adverse effects
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology
  • Macrophages / drug effects
  • Microglia / drug effects
  • Oximes / adverse effects
  • Oximes / chemical synthesis*
  • Oximes / chemistry
  • Oximes / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Indoles
  • Oximes