title: Synthesis and cytotoxic evaluation of combretafurans, potential scaffolds for dual-action antitumoral agents.
abstract: We have synthesized rigid analogues of combretastatin bearing a furan ring in place of the olefinic bridge. These compounds are cytotoxic at nanomolar concentrations in neuroblastoma cells, display a similar structure-activity relationship compared to combretastatin A4, and inhibit tubulin polymerization. We also show that the furan ring can be further functionalized. Thus, it is possible that combretafurans could act as scaffolds for the development of dual-action antitumoral agents.
authors.affiliation: Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale A. Avogadro, Via Bovio 6, 28100 Novara, Italy.
authors.forename: Tracey
authors.initials: T
authors.lastname: Pirali
authors.forename: Sara
authors.initials: S
authors.lastname: Busacca
authors.forename: Lorena
authors.initials: L
authors.lastname: Beltrami
authors.forename: Daniela
authors.initials: D
authors.lastname: Imovilli
authors.forename: Francesca
authors.initials: F
authors.lastname: Pagliai
authors.forename: Gianluca
authors.initials: G
authors.lastname: Miglio
authors.forename: Alberto
authors.initials: A
authors.lastname: Massarotti
authors.forename: Luisella
authors.initials: L
authors.lastname: Verotta
authors.forename: Gian Cesare
authors.initials: GC
authors.lastname: Tron
authors.forename: Giovanni
authors.initials: G
authors.lastname: Sorba
authors.forename: Armando A
authors.initials: AA
authors.lastname: Genazzani
mesh_terms: D000840:Anisoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001632:Bibenzyls / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009447:Neuroblastoma / Q000188:drug therapy*; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000187:drug effects
chemical_list: D000840:Anisoles; D000970:Antineoplastic Agents; D001632:Bibenzyls; D005663:Furans; D013267:Stilbenes; D014404:Tubulin; C040105:combretastatin; C058728:fosbretabulin; C039281:furan