348597-81-9Relevant articles and documents
Design, Synthesis, and Biological Characterization of Metabolically Stable Selective Androgen Receptor Modulators
Marhefka, Craig A.,Gao, Wenqing,Chung, Kiwon,Kim, Juhyun,He, Yali,Yin, Donghua,Bohl, Casey,Dalton, James T.,Miller, Duane D.
, p. 993 - 998 (2004)
A series of nonsteroidal ligands were synthesized as second-generation agonists for the androgen receptor (AR). These ligands were designed to eliminate metabolic sites identified in one of our first-generation AR agonists, which was inactive in vivo due
Novel pathway for the synthesis of arylpropionamide-derived selective androgen receptor modulator (SARM) metabolites of andarine and ostarine
Schragl, Katharina M.,Forsdahl, Guro,Gmeiner, Guenter,Enev, Valentin S.,Gaertner, Peter
supporting information, p. 2239 - 2242 (2013/05/09)
O-Dephenylandarine and O-dephenylostarine, two SARM metabolites relevant for doping control analysis, were synthesized in their endogenous (S)-forms as well as in terms of their racemates. The enantiopure (S)-metabolites were obtained after six steps in 20% and 23% overall yield, the slightly modified racemic route provided the compounds in 28% and 31% total yield, respectively.
Effect of B-ring substitution pattern on binding mode of propionamide selective androgen receptor modulators
Bohl, Casey E.,Wu, Zengru,Chen, Jiyun,Mohler, Michael L.,Yang, Jun,Hwang, Dong Jin,Mustafa, Suni,Miller, Duane D.,Bell, Charles E.,Dalton, James T.
supporting information; experimental part, p. 5567 - 5570 (2009/06/30)
Selective androgen receptor modulators (SARMs) are essentially prostate sparing androgens, which provide therapeutic potential in osteoporosis, male hormone replacement, and muscle wasting. Herein we report crystal structures of the androgen receptor (AR) ligand-binding domain (LBD) complexed to a series of potent synthetic nonsteroidal SARMs with a substituted pendant arene referred to as the B-ring. We found that hydrophilic B-ring para-substituted analogs exhibit an additional region of hydrogen bonding not seen with steroidal compounds and that multiple halogen substitutions affect the B-ring conformation and aromatic interactions with Trp741. This information elucidates interactions important for high AR binding affinity and provides new insight for structure-based drug design.
