title: Homopterocarpanes as bridged triarylethylene analogues: synthesis and antagonistic effects in human MCF-7 breast cancer cells.
abstract: A series of new compounds structurally derived from 6a,12a-dihydro-6H,7H-[1]-benzopyran-[4,3-b]-benzopyran (homopterocarpane) was efficiently synthesized by reduction of the corresponding pyrilium salts obtained by treatment of selected flavanones and aldehydes with anhydrous HClO4. Cytotoxic effects on the human breast cancer cell line MCF-7 and antiestrogenic activity (only for compounds which resulted more active than tamoxifen (TAM)) on MCF-7 cells stimulated by 17beta-estradiol were evaluated. In vivo antiestrogenic activity and the relative binding affinity were also assessed. Some of the new compounds (4c, 4h, 4i and 4l) showed a biological activity in the micromolar range, and were more potent than TAM taken as the reference.
authors.affiliation: Department of Pharmaceutical Sciences, University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy. angela.rampa@unibo.it
authors.forename: Angela
authors.initials: A
authors.lastname: Rampa
authors.forename: Alessandra
authors.initials: A
authors.lastname: Bisi
authors.forename: Federica
authors.initials: F
authors.lastname: Belluti
authors.forename: Silvia
authors.initials: S
authors.lastname: Gobbi
authors.forename: Lorna
authors.initials: L
authors.lastname: Piazzi
authors.forename: Piero
authors.initials: P
authors.lastname: Valenti
authors.forename: Antonella
authors.initials: A
authors.lastname: Zampiron
authors.forename: Anna
authors.initials: A
authors.lastname: Caputo
authors.forename: Katia
authors.initials: K
authors.lastname: Varani
authors.forename: Pier Andrea
authors.initials: PA
authors.lastname: Borea
authors.forename: Maria
authors.initials: M
authors.lastname: Carrara
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001665:Binding Sites; D001943:Breast Neoplasms / Q000473:pathology; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D004958:Estradiol / Q000494:pharmacology; D005030:Ethylenes / Q000737:chemistry*; D005260:Female; D044950:Flavanones / Q000737:chemistry; D006801:Humans; D036343:Pterocarpans / Q000737:chemistry*; D011960:Receptors, Estrogen / Q000187:drug effects
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D005030:Ethylenes; D044950:Flavanones; D036343:Pterocarpans; D011960:Receptors, Estrogen; D004958:Estradiol