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

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 C_17,20-lyase inhibitors

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

Unite de recherche en chimie physique, theorique et structurale

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

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 C_17,20-lyase activity and displayed moderate inhibitory effect.

langue originale	Anglais
Pages (de - à)	61-66
Nombre de pages	6
journal	Steroids
Volume	123
Les DOIs	https://doi.org/10.1016/j.steroids.2017.05.006
Etat de la publication	Publié - 1 juil. 2017

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10.1016/j.steroids.2017.05.006

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Physico-chimie et caractérisation (PC2)
Johan Wouters (!!Manager) & Carmela Aprile (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique

CCDC 1520874: Experimental Crystal Structure Determination
Gömöry, Á. (Contributeur), Edina Herman, B. (Contributeur), Kollár, L. (Contributeur), Maksó, L. (Contributeur), Mikle, G. (Contributeur), Skoda-Földes, R. (Contributeur), Szánti-Pintér, E. (Contributeur), Szécsi, M. (Contributeur) & Wouters, J. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2017
DOI: 10.5517/ccdc.csd.cc1n1lgr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n1lgr&sid=DataCite
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Contient cette citation

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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",

year = "2017",

month = jul,

day = "1",

doi = "10.1016/j.steroids.2017.05.006",

language = "English",

volume = "123",

pages = "61--66",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C17,20-lyase inhibitors

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

PY - 2017/7/1

Y1 - 2017/7/1

N2 - 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.

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.

KW - 16-Dehydropregnenolone

KW - Aza-Michael addition

KW - DBU

KW - Ionic liquid

KW - P450 inhibitors

UR - http://www.scopus.com/inward/record.url?scp=85019870573&partnerID=8YFLogxK

U2 - 10.1016/j.steroids.2017.05.006

DO - 10.1016/j.steroids.2017.05.006

M3 - Article

AN - SCOPUS:85019870573

SN - 0039-128X

VL - 123

SP - 61

EP - 66

JO - Steroids

JF - Steroids

ER -

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

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Ensembles de données

CCDC 1520874: Experimental Crystal Structure Determination

Contient cette citation

Synthesis of 16α-amino-pregnenolone derivatives via ionic liquid-catalyzed aza-Michael addition and their evaluation as C_17,20-lyase inhibitors