Synthesis, Structure, and Biological Properties of Some 8α Analogues of Steroid Estrogens with Fluorine in Position 2

V. N. Belov1, V. Yu. Dudkin1, E. A. Urusova1, G. L. Starova1, S. I. Selivanov1, S. V. Nikolaev1, N. D. Eshchenko1, S. N. Morozkina1 and A. G. Shavva1 #

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1Faculty of Chemistry, St. Petersburg State University, Universitetskii pr. 26, Staryi Petergof, St. Petersburg, 198504, Russia

Received: August  5, 2006; in final form: November  28, 2006

Abstract.  A total synthesis of 8α analogues of steroid estrogens with fluorine in position 2 was achieved. Structural features of these compounds were studied by the example of 17β-acetoxy-2-fluoro-3-methoxy-8α-estra-1,3,5(10)-triene. It was shown that the 8α analogues of 2-fluorosubstituted steroid estrogens have a low uterotropic activity and retain the osteoprotective and hypocholesterolemic activities.

Key words:  2-F-analogues, hormone replacement therap,- molecular structure, steroid estrogens, total synthesis

Russian Journal of Bioorganic Chemistry 2007, 33 (3): 293-301