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 #
#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