Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors
| Autor: | Johan Wouters, Mihály Szécsi, Rita Skoda-Földes, Gábor Mikle, Lilla Maksó, László Kollár, Bianka Edina Herman, Eszter Szánti-Pintér, Ágnes Gömöry |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
C17 20 lyase
Clinical Biochemistry DBU Ionic liquid 010402 general chemistry 01 natural sciences Biochemistry Catalysis chemistry.chemical_compound Endocrinology medicine Organic chemistry Molecular Biology Aza-Michael addition Pharmacology 010405 organic chemistry Organic Chemistry Carbon-13 NMR Recyclable catalyst 0104 chemical sciences Solvent chemistry Pregnenolone Michael reaction 16-Dehydropregnenolone P450 inhibitors medicine.drug |
| Zdroj: | Steroids. 123:61-66 |
| ISSN: | 0039-128X |
| DOI: | 10.1016/j.steroids.2017.05.006 |
| Popis: | Aza-Michael addition of 16-dehydropregnenolone was studied in the presence of a basic ionic liquid, [DBU][OAc] as catalyst and solvent. The reaction was carried out using different primary and secondary amines as N-nucleophiles. The products were obtained in moderate to good yields and were characterized by 1H and 13C NMR, MS and IR. The ionic liquid was found to be an efficient and recyclable catalyst that was reused five times. The products were investigated for the inhibition of in vitro C17,20-lyase activity and displayed moderate inhibitory effect. |
| Databáze: | OpenAIRE |
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