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 H and C 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-lyase activity and displayed moderate inhibitory effect.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.steroids.2017.05.006DOI Listing

Publication Analysis

Top Keywords

aza-michael addition
8
ionic liquid
8
synthesis 16α-amino-pregnenolone
4
16α-amino-pregnenolone derivatives
4
derivatives ionic
4
ionic liquid-catalyzed
4
liquid-catalyzed aza-michael
4
addition evaluation
4
evaluation c-lyase
4
c-lyase inhibitors
4

Similar Publications

Expression of concern for 'Graphene oxide: an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes' by Sanny Verma , , 2011, , 12673-12675, https://doi.org/10.1039/C1CC15230K.

View Article and Find Full Text PDF

This study presents the synthesis of a Cd(II) based hydrophobic three dimensional crystalline network material (CNM), [Cd(L)(LH)(bpe)], {L = {4,4'-(hexafluroisopropylidine)bis(benzoate)} and 1,2-di(4-pyridyl) ethylene (bpe)}, 1(Cd), by employing the slow-diffusion method. The three-dimensional structure of 1(Cd) was determined by single crystal X-ray diffraction and characterized by powder X-ray diffraction (PXRD), FT-IR spectroscopy and thermogravimetric analysis (TGA). Subsequently, post-synthetic modification of 1(Cd) with Cu(II) at room temperature led to the formation of isostructural 1(Cu) with partial substitution.

View Article and Find Full Text PDF

Exploiting photopolymerization to modulate liquid crystalline network actuation.

Soft Matter

January 2025

LENS (European Laboratory for Non-Linear Spectroscopy) Via Nello Carrara 1, 50019 Sesto Fiorentino (FI), Italy.

Liquid Crystalline Networks (LCNs) are widely investigated to develop actuators, from soft robots to artificial muscles. Indeed, they can produce forces and movements in response to a plethora of external stimuli, showing kinetics up to the millisecond time-scale. One of the most explored preparation technique involves the photopolymerization of an aligned layer of reactive mesogens.

View Article and Find Full Text PDF

Diastereoselective Construction of Bridged Azabicyclo[3.2.1]octane via Copper-Catalyzed Formal [4 + 3] Cycloaddition.

J Org Chem

January 2025

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.

A novel copper-catalyzed formal diastereoselective [4 + 3] cycloaddition of 2-arylaziridines and 2-substituted cyclopentadiene was developed. This transformation provided an efficient protocol for the assembly of a highly strained bridged azabicyclo[3.2.

View Article and Find Full Text PDF

Asymmetric Total Syntheses of Sarglamides A, C, and E.

J Org Chem

January 2025

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 Gansu, P. R. China.

The asymmetric total syntheses of sarglamides A, C, and E in concise and protecting group free fashion is disclosed. Key steps involve an -selective Diels-Alder reaction to construct the bicyclo[2.2.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!