5255-17-4Relevant academic research and scientific papers
Marine and semi-synthetic hydroxysteroids as new scaffolds for pregnane X receptor modulation
Sepe, Valentina,Di Leva, Francesco Saverio,D'Amore, Claudio,Festa, Carmen,De Marino, Simona,Renga, Barbara,D'Auria, Maria Valeria,Novellino, Ettore,Limongelli, Vittorio,D'Souza, Lisette,Majik, Mahesh,Zampella, Angela,Fiorucci, Stefano
, p. 3091 - 3115 (2014/07/08)
In recent years many sterols with unusual structures and promising biological profiles have been identified from marine sources. Here we report the isolation of a series of 24-alkylated-hydroxysteroids from the soft coral Sinularia kavarattiensis, acting as pregnane X receptor (PXR) modulators. Starting from this scaffold a number of derivatives were prepared and evaluated for their ability to activate the PXR by assessing transactivation and quantifying gene expression. Our study reveals that ergost-5-en-3β-ol (4) induces PXR transactivation in HepG2 cells and stimulates the expression of the PXR target gene CYP3A4. To shed light on the molecular basis of the interaction between these ligands and PXR, we investigated, through docking simulations, the binding mechanism of the most potent compound of the series, 4, to the PXR. Our findings provide useful functional and structural information to guide further investigations and drug design.
A new route for synthesizing cholesterol analogs with fluorocarbon side chains and their liquid-crystalline aliphatic esters
Shen, Yuehai,Wen, Jianxun
, p. 13 - 15 (2007/10/03)
A new and efficient route has been developed to synthesize 17β-(1-methyl-3-perfluoroalkyl)propyl-3β-androsterol (1) in nine steps from hyodeoxycholic acid via selective addition of 1-perfluoroalkyl iodide to 24-norchola-5,22-dien-3β-ol. From (1), the first series of steroidal liquid crystalline aliphatic esters (smectic A) with fluorocarbon side chains has been prepared.

