title: A facile synthesis of C(2)-symmetric 17 beta-estradiol dimers.
abstract: A rapid and efficient synthesis of a series of C(2)-symmetric 17 beta-estradiol dimers is described. The new molecules are linked at position 17 alpha of the steroid nucleus with either an alkyl chain or a polyethylene glycol chain. They are made from estrone in five chemical steps with an overall yield exceeding 30%. The biological activity of these compounds was evaluated in vitro on estrogen dependent and independent (ER(+) and ER(-)) human breast tumor cell lines: MCF-7 and MDA-MB-231. Some of the dimers present selective cytotoxic activity against the ER(+) cell line.
authors.affiliation: Département de Chimie-Biologie, Université du Québec à Trois-Rivières, C.P. 500, Trois-Rivières, Québec, Canada G9A 5H7.
authors.forename: Daniel
authors.initials: D
authors.lastname: Rabouin
authors.forename: Valérie
authors.initials: V
authors.lastname: Perron
authors.forename: Blaise
authors.initials: B
authors.lastname: N'Zemba
authors.forename: René
authors.initials: R
authors.lastname: C-Gaudreault
authors.forename: Gervais
authors.initials: G
authors.lastname: Bérubé
mesh_terms: D000478:Alkylation; D001667:Binding, Competitive / Q000187:drug effects; D001943:Breast Neoplasms / Q000378:metabolism; D003124:Colorimetry; D004396:Coloring Agents; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D004970:Estrone / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D006801:Humans; D011092:Polyethylene Glycols; D011960:Receptors, Estrogen / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D004396:Coloring Agents; D011960:Receptors, Estrogen; D004970:Estrone; D011092:Polyethylene Glycols; D004958:Estradiol