A facile synthesis of C(2)-symmetric 17 beta-estradiol dimers

Bioorg Med Chem Lett. 2003 Feb 10;13(3):557-60. doi: 10.1016/s0960-894x(02)00987-3.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Binding, Competitive / drug effects
  • Breast Neoplasms / metabolism
  • Colorimetry
  • Coloring Agents
  • Estradiol / analogs & derivatives*
  • Estradiol / chemical synthesis*
  • Estradiol / pharmacology
  • Estrone / chemical synthesis
  • Estrone / pharmacology
  • Female
  • Humans
  • Polyethylene Glycols
  • Receptors, Estrogen / drug effects
  • Receptors, Estrogen / metabolism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Coloring Agents
  • Receptors, Estrogen
  • Estrone
  • Polyethylene Glycols
  • Estradiol