title: Novel A-ring and B-ring modified combretastatin A-4 (CA-4) analogues endowed with interesting cytotoxic activity.
abstract: A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Ferrara, Ferrara, Italy. smd@unife.it
authors.forename: Daniele
authors.initials: D
authors.lastname: Simoni
authors.forename: Romeo
authors.initials: R
authors.lastname: Romagnoli
authors.forename: Riccardo
authors.initials: R
authors.lastname: Baruchello
authors.forename: Riccardo
authors.initials: R
authors.lastname: Rondanin
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Grisolia
authors.forename: Marco
authors.initials: M
authors.lastname: Eleopra
authors.forename: Michele
authors.initials: M
authors.lastname: Rizzi
authors.forename: Manlio
authors.initials: M
authors.lastname: Tolomeo
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Giannini
authors.forename: Domenico
authors.initials: D
authors.lastname: Alloatti
authors.forename: Massimo
authors.initials: M
authors.lastname: Castorina
authors.forename: Marcella
authors.initials: M
authors.lastname: Marcellini
authors.forename: Claudio
authors.initials: C
authors.lastname: Pisano
mesh_terms: D000818:Animals; D001665:Binding Sites; D002417:Cattle; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D042783:Endothelial Cells / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000187:drug effects / Q000378:metabolism
chemical_list: D013267:Stilbenes; D014404:Tubulin; C529077:cis-3,4',5-trimethoxy-3'-aminostilbene; C058728:fosbretabulin