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. Shavva^1 #

^#Phone: (812) 428-68-09; fax: (812) 428-69-39; e-mail: AGShavva@yandex.ru

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