Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors

Eszter Szánti-Pintér, Lilla Maksó, Ágnes Gömöry, Johan Wouters, Bianka Edina Herman, Mihály Szécsi, Gábor Mikle, László Kollár, Rita Skoda-Földes

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)61-66
Number of pages6
JournalSteroids
Volume123
DOIs
Publication statusPublished - 1 Jul 2017

Fingerprint

Ionic Liquids
Pregnenolone
Lyases
Derivatives
Nucleophiles
Catalysts
Amines
Nuclear magnetic resonance
16-pregnolone
16-dehydropregnenolone
In Vitro Techniques
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • 16-Dehydropregnenolone
  • Aza-Michael addition
  • DBU
  • Ionic liquid
  • P450 inhibitors

Cite this

Szánti-Pintér, Eszter ; Maksó, Lilla ; Gömöry, Ágnes ; Wouters, Johan ; Edina Herman, Bianka ; Szécsi, Mihály ; Mikle, Gábor ; Kollár, László ; Skoda-Földes, Rita. / Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors. In: Steroids. 2017 ; Vol. 123. pp. 61-66.
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abstract = "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.",
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Szánti-Pintér, E, Maksó, L, Gömöry, Á, Wouters, J, Edina Herman, B, Szécsi, M, Mikle, G, Kollár, L & Skoda-Földes, R 2017, 'Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors', Steroids, vol. 123, pp. 61-66. https://doi.org/10.1016/j.steroids.2017.05.006

Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors. / Szánti-Pintér, Eszter; Maksó, Lilla; Gömöry, Ágnes; Wouters, Johan; Edina Herman, Bianka; Szécsi, Mihály; Mikle, Gábor; Kollár, László; Skoda-Földes, Rita.

In: Steroids, Vol. 123, 01.07.2017, p. 61-66.

Research output: Contribution to journalArticle

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AU - Szánti-Pintér, Eszter

AU - Maksó, Lilla

AU - Gömöry, Ágnes

AU - Wouters, Johan

AU - Edina Herman, Bianka

AU - Szécsi, Mihály

AU - Mikle, Gábor

AU - Kollár, László

AU - Skoda-Földes, Rita

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