2-Arylindenes and 2-Arylindenones: Synthesis of Probes To Study the Binding Orientation of Unsymmetrical Nonsteroidal Ligands to the Estrogen Receptor

Gregory M. Anstead, Jean L. Ensign, Chad S. Peterson, John A. Katzenellenbogen

Resultado de la investigación: Articlerevisión exhaustiva

53 Citas (Scopus)

Resumen

A set of 2-arylindene and -indenone systems, bearing a 3-ethyl or 3-aryl substituent and a single hydroxyl group either on the 6-position of the indene or 4'-position of the C-2 aryl group, have been synthesized in connection with a larger investigation of the orientation with which 2-arylindene nonsteroidal estrogens bind to the estrogen receptor. The 6-hydroxyl-substituted systems are prepared by a-benzylation or benzoylation of a benzyl ketone, followed by Friedel-Crafts cyclization to the indene or indenone. The 2-(4-hydroxyphenyl)-substituted systems were approached via a 2-arylindan-l,3-dione: Grignard addition-dehydration gave the corresponding indenones from which the indenes could be prepared by Wolff-Kishner reduction. 1,3-Diethyl-2-(4-hydroxyphenyl)indene was prepared by hydride reduction of a benzofulvene precursor. The molecular structures and estrogen receptor binding affinities of these 2-arylindene and -indenone systems will be presented elsewhere.

Idioma originalEnglish (US)
Páginas (desde-hasta)1485-1491
Número de páginas7
PublicaciónJournal of Organic Chemistry
Volumen54
N.º7
DOI
EstadoPublished - mar. 1 1989
Publicado de forma externa

ASJC Scopus subject areas

  • Organic Chemistry

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