The use of doping in sports is a global problem that affects athletes around the world. Among the different methods developed to detect doping agents in biological samples, there are antibody-based methods that need an appropriate hapten design. Steroids with a hydroxyl group can be converted to the corresponding hemisuccinates. A novel approach to the synthesis of 17β-O-hemisuccinate of the common doping agent stanozolol is described here. Acylation of stanozolol with methyl 4-chloro-4-oxobutyrate/4-dimethylaminopyridine, followed by mild alkaline hydrolysis with methanolic sodium hydroxide at room temperature, gave the simultaneous protection and deprotection of pyrazole-nitrogen atoms. The proposed new synthetic method allows the desired hemisuccinate derivative to be obtained in only two steps, and with a good total yield starting from stanozolol.
Simple Synthesis of 17-β-O-hemisuccinate of Stanozolol for Immunoanalytical Methods / S. Casati, R. Ottria, P. Ciuffreda. - In: MOLECULES. - ISSN 1420-3049. - 25:9(2020 Apr), pp. 2019.1-2019.9.
|Titolo:||Simple Synthesis of 17-β-O-hemisuccinate of Stanozolol for Immunoanalytical Methods|
CIUFFREDA, PIERANGELA (Corresponding)
|Parole Chiave:||steroids; stanozolol; metabolism; synthesis; anabolic–androgenic steroid|
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||apr-2020|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/molecules25092019|
|Appare nelle tipologie:||01 - Articolo su periodico|