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

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

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

Original language	English
Pages (from-to)	61-66
Number of pages	6
Journal	Steroids
Volume	123
DOIs	https://doi.org/10.1016/j.steroids.2017.05.006
Publication status	Published - 1 Jul 2017

Keywords

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

Access to Document

10.1016/j.steroids.2017.05.006

Cite this

@article{77ed7d4ab36d45819f7b694b31acda5c,

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",

}

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 C_17,20-lyase inhibitors

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Physical Chemistry and characterization(PC2)

CCDC 1520874: Experimental Crystal Structure Determination

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Equipment

Physical Chemistry and characterization(PC2)

Datasets

CCDC 1520874: Experimental Crystal Structure Determination

Cite this

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