title: Hetero-Diels-Alder approach to Bis(indolyl)methanes.
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.
authors.affiliation: CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal.
authors.forename: Carla
authors.initials: C
authors.lastname: Grosso
authors.affiliation: CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal.
authors.forename: Ana L
authors.initials: AL
authors.lastname: Cardoso
authors.affiliation: CCMAR, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
authors.forename: Maria João
authors.initials: MJ
authors.lastname: Rodrigues
authors.affiliation: CCMAR, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
authors.forename: Cátia
authors.initials: C
authors.lastname: Marques
authors.affiliation: CCMAR, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
authors.forename: Luísa
authors.initials: L
authors.lastname: Barreira
authors.affiliation: CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal; FCT, University of Algarve, Campus de Gambelas, 8005-139 Faro, Portugal.
authors.forename: Américo
authors.initials: A
authors.lastname: Lemos
authors.affiliation: CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. Electronic address: tmelo@ci.uc.pt.
authors.forename: Teresa M D V
authors.initials: TMDV
authors.lastname: Pinho E Melo
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D061565:Cycloaddition Reaction; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D008697:Methane
keywords: Anti-cancer activity; Azoalkenes; Bis(indolyl)methanes; Hetero-Diels-Alder reaction; Indoles; Leukaemia; Lymphoma; Nitrosoalkenes