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

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

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.

langueAnglais
Pages61-66
Nombre de pages6
journalSteroids
Volume123
Les DOIs
étatPublié - 1 juil. 2017

Empreinte digitale

Steroid 17-alpha-Hydroxylase
Ionic Liquids
Pregnenolone
Lyases
Derivatives
Nucleophiles
Catalysts
Amines
Nuclear magnetic resonance
16-dehydropregnenolone
In Vitro Techniques

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    Szánti-Pintér, E., Maksó, L., Gömöry, Á., Wouters, J., Edina Herman, B., Szécsi, M., ... 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, 123, 61-66. DOI: 10.1016/j.steroids.2017.05.006
    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. Dans: Steroids. 2017 ; Vol 123. p. 61-66
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    title = "Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors",
    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.",
    keywords = "16-Dehydropregnenolone, Aza-Michael addition, DBU, Ionic liquid, P450 inhibitors",
    author = "Eszter Sz{\'a}nti-Pint{\'e}r and Lilla Maks{\'o} and {\'A}gnes G{\"o}m{\"o}ry and Johan Wouters and {Edina Herman}, Bianka and Mih{\'a}ly Sz{\'e}csi and G{\'a}bor Mikle and L{\'a}szl{\'o} Koll{\'a}r and Rita Skoda-F{\"o}ldes",
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    doi = "10.1016/j.steroids.2017.05.006",
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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, p. 61-66. DOI: 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.

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

    Résultats de recherche: Contribution à un journal/une revueArticle

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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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    AB - 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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    KW - Ionic liquid

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