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.
Carla Grosso  1 ,  Ana Lúcia Cardoso  2 ,  Américo Lemos  3 ,  João Varela  4 ,  Maria João Rodrigues  4 ,  Luísa Custódio  4 ,  Luísa Barreira  4 ,  Teresa M V D Pinho e Melo  5
Affiliations
  • 1. Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal; CIQA, FCT, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
  • 2. Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal.
  • 3. CIQA, FCT, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal. Electronic address: [email protected].
  • 4. CCMAR-Centre of Marine Sciences, Faculty of Sciences and Technology, University of Algarve, Ed. 7, Campus of Gambelas, Faro 8005-139, Portugal.
  • 5. Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. Electronic address: [email protected].
PMID: 25644672 DOI: 10.1016/j.ejmech.2015.01.050
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.