Anabolic and androgenic activities of 19-nor-testosterone steroids: QSAR study using quantum and physicochemical molecular descriptors

Quantitative structure-activity relationship (QSAR) study of 19-nor-testosterone steroids family was performed using quantum and physicochemical molecular descriptors. The quantum-chemical descriptors were calculated using semiempirical calculations. The descriptor values were statistically correlated using multi-linear regression analysis. The QSAR study indicated that the electronic properties of these derivatives have significant relationship with observed biological activities. The found QSAR equations explain that the energy difference between the LUMO and HOMO, the total dipole moment, the chemical potential and the value of the net charge of different carbon atoms in the steroid nucleus showed key interaction of these steroids with their anabolic-androgenic receptor binding site. The calculated values predict that the 17α-cyclopropyl-17β, 3β-hydroxy-4-estrene compound presents the highest anabolic-androgenic ratio (AAR) and the 7α-methyl-17β-acetoxy-estr-4-en-3-one compound the lowest AAR. This study might be helpful in the future successful identification of >real> or >virtual> anabolic-androgenic steroids. © 2011 Elsevier Ltd. All rights reserved.Most of the authors are indebted to the Universidad de La Habana, Cuba, for the overall support of their education and work. The Universidad Autónoma de Madrid served as excellent host for the essential part of this work as well as the Spanish Agency for International Cooperation for Development (D/019558/08 and D/023653/09) funding. JMGV is grateful for support from MEC of Spain (CTQ 2007-63332 and CTQ2010-19232).Peer Reviewe