Structural elucidation of major selective androgen receptor modulator (SARM) metabolites for doping control
Selective androgen receptor modulators (SARMs) are a class of androgen receptor drugs, which have a high potential to be performance enhancers in human and animal sports. Arylpropionamides are one of the major SARM classes and get rapidly metabolized significantly complicating simple detection of misconduct in blood or urine sample analysis. Specific drug-derived metabolites are required as references due to a short half-life of the parent compound but are generally lacking. The difficulty in metabolism studies is the determination of the correct regio and stereoselectivity during metabolic conversion processes. In this study, we have elucidated and verified the chemical structure of two major equine arylpropionamide-based SARM metabolites using a combination of chemical synthesis and liquid chromatography-mass spectrometry (LC-MS) analysis. These synthesized SARM-derived metabolites can readily be utilized as reference standards for routine mass spectrometry-based doping control analysis of at least three commonly used performance-enhancing drugs to unambigously identify misconduct.
Garg, Neeraj,Hansson, Annelie,Knych, Heather K.,Stanley, Scott D.,Thevis, Mario,Bondesson, Ulf,Hedeland, Mikael,Globisch, Daniel
supporting information
p. 698 - 702
(2018/02/09)
The discovery of a potent orally efficacious indole androgen receptor antagonist through in vivo screening
A series of novel 2-(1H-indol-2-yl)-propan-2-ols have been designed, synthesized, and screened for their ability to inhibit testosterone-induced prostate weight increases in immature rats. Through the use of this paradigm, we were able to identify compoun
Lanter, James C.,Fiordeliso, James J.,Jiang, Weiqin,Allan, George F.,Lai, Muh-Tsann,Linton, Olivia,Hahn, Do Won,Lundeen, Scott G.,Sui, Zhihua
p. 123 - 126
(2007/10/03)
A bioisosteric approach to the discovery of indole carbinol androgen receptor ligands
Two potential bioisosteres of the nonsteroidal antiandrogen bicalutamide, an imidazolidinone and an indole, were synthesized and tested for their androgen receptor binding. Indole was discovered to be a suitable bioisostere for the acyl anilide moiety in the parent compound. Several analogs in the indole series were found to be 10-fold better than bicalutamide in binding to the recombinant androgen receptor binding domain.
Lanter, James C.,Fiordeliso, James J.,Allan, George F.,Musto, Amy,Hahn, Do Won,Sui, Zhihua
p. 5646 - 5649
(2007/10/03)
Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols
(Chemical Equation Presented) The tetrahydro-pyrano[3,4-b]indoles 6 were synthesized from 2-(2-trimethylsilanyl-1H-indol-3-yl)-ethanols 5 and various ketones or aldehydes through silicon-directed oxa-Pictet-Spengler cyclizations. An unusual reaction led to the dimeric products 7 when some of 5 was treated with acetone using BF3 as the catalyst.
Zhang, Xuqing,Li, Xiaojie,Lanter, James C.,Sui, Zhihua
p. 2043 - 2046
(2007/10/03)
Novel indole derivatives as selective androgen receptor modulators (SARMS)
The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.
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Page/Page column 38-39
(2008/06/13)
NOVEL INDOLE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATOR (SARMS)
The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.
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Page/Page column 38-39
(2008/06/13)
Novel indole derivatives as selective androgen receptor modulators (SARMS)
The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.
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Page/Page column 39-40
(2010/02/14)
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