Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods
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...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/9/2019 |
| _version_ | 1827717951332024320 |
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| author | Silvana Casati Roberta Ottria Pierangela Ciuffreda |
| author_facet | Silvana Casati Roberta Ottria Pierangela Ciuffreda |
| author_sort | Silvana Casati |
| collection | DOAJ |
| description | 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-<i>O</i>-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. |
| first_indexed | 2024-03-10T20:13:13Z |
| format | Article |
| id | doaj.art-8b9d39eac656462499653dd2c627f9b7 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T20:13:13Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8b9d39eac656462499653dd2c627f9b72023-11-19T22:46:30ZengMDPI AGMolecules1420-30492020-04-01259201910.3390/molecules25092019Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical MethodsSilvana Casati0Roberta Ottria1Pierangela Ciuffreda2Dipartimento di Scienze Biomediche e Cliniche “Luigi Sacco”, Università degli Studi di Milano, Via G.B. Grassi 74, 20157 Milano, ItalyDipartimento di Scienze Biomediche e Cliniche “Luigi Sacco”, Università degli Studi di Milano, Via G.B. Grassi 74, 20157 Milano, ItalyDipartimento di Scienze Biomediche e Cliniche “Luigi Sacco”, Università degli Studi di Milano, Via G.B. Grassi 74, 20157 Milano, ItalyThe 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-<i>O</i>-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.https://www.mdpi.com/1420-3049/25/9/2019steroidsstanozololmetabolismsynthesisanabolic–androgenic steroid |
| spellingShingle | Silvana Casati Roberta Ottria Pierangela Ciuffreda Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods Molecules steroids stanozolol metabolism synthesis anabolic–androgenic steroid |
| title | Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods |
| title_full | Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods |
| title_fullStr | Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods |
| title_full_unstemmed | Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods |
| title_short | Simple Synthesis of 17-β-<i>O</i>-hemisuccinate of Stanozolol for Immunoanalytical Methods |
| title_sort | simple synthesis of 17 β i o i hemisuccinate of stanozolol for immunoanalytical methods |
| topic | steroids stanozolol metabolism synthesis anabolic–androgenic steroid |
| url | https://www.mdpi.com/1420-3049/25/9/2019 |
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