2. Academic Validation
  3. Hetero-Diels-Alder approach to Bis(indolyl)methanes

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

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: tmelo@ci.uc.pt.
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.

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