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.
Carla Grosso  1 ,  Ana L Cardoso  1 ,  Maria João Rodrigues  2 ,  Cátia Marques  2 ,  Luísa Barreira  2 ,  Américo Lemos  3 ,  Teresa M D V Pinho E Melo  4
Affiliations
  • 1. CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal.
  • 2. CCMAR, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
  • 3. CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal; FCT, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
  • 4. CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. Electronic address: [email protected].
PMID: 28062194 DOI: 10.1016/j.bmc.2016.12.028
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.