Ergogenics   [Definitie:] "An ergogenic aid is any substance or phenomenon that enhances performance." (Wilmore and Costill)   Nieuwsbrief over doping, supplementen, voeding en training
Vergeten doping       Anabolica-studies       Risico's van anabolica       In de pijplijn

1 4 - 0 7 - 2 0 0 5 Synthesis of an Androgenic-Anabolic Nonsteroid Gala Zanati, Manfred Wolff. Department of Pharmaceutical Chemistry, School of Pharmacy University of California, San Francisco Received August 7, 1972 Journal of Medicinal Chemistry, 1973, Vol. 16, No. I Sir: We describe the synthesis of tricyclic compounds corresponding to steroids lacking ring A which have significant androgenic activity. This finding is of importance in connection with the question of whether the intact steroid nucleusis a sine qua non for the production of various kinds of hormonal effects. Numerous synthetic estrogens lacking the steroid nucleus have been synthesized, and have found utility as drugs for contraceptive, antineoplastic, and obstetrical purposes, but attempts to find similar agents in the androgens have produced only inactive compounds or compounds having only 1-2% of the activity of testosterone. Our recent studies on the structural requirements in the A ring of steroids for androgenic action indicated that only the steric, and not the electronic, characteristics of ring A are important in eliciting this biological response. Therefore, it appeared feasible to prepare a nonsteroidal androgen lacking an A ring but in which hydrogen atoms of methyl groups at C-10 and C-5 would replace the carbon atoms at C-2 and C-3. In such a compound, the conformation of the carbon atoms of the C-5 and C-10 methyl groups is fixed because of the relatively inflexible nature of the condensed tricyclic ring system and although the hydrogen atoms may assume a variety of conformations, the most stable is a staggered chair-like structure placing hydrogen atoms in the approximate vicinity of C-2 and C-3 in ring A. Biological examination was carried out by injecting the compounds as suspensions in carboxymethyl cellulose solution to castrate rats for 7 consecutive days with autopsy on the day after the last treatment day. Testing was done at Endocrine Laboratories, Madison, Wis. The organ weights obtained are shown in Table I. Our data show that compound 1 has anabolic (levator ani) activity in the range of clinically useful compounds with low androgenic (ventral prostate and seminal vesicle) activity. Similarly, the 17beta-acetate and the 17alpha-methyl derivatives exhibit corresponding activity, while enhancement of potency is obtained by introduction of the 7alpha-methyl group analogous to the case in testosterone. If the activity of 1 is, in fact, due to the spatial relationship of two hydrogens approximating the position of C-2 and C-3, one would expect that derivatives 5 and 6 having methylene groups in place of methyl groups would lack activity and this was confirmed by the results. [Link]

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