Pregna-5,17(20)-dien-21-oyl amides affecting sterol and triglyceride biosynthesis in Hep G2 cells.

Abstract

Synthesis of series [17(20)Z]- and [17(20)E]-pregna-5,17(20)-dien-21-oyl amides, containing polar substituents in amide moiety, based on rearrangement of 17α-bromo-21-iodo-3β-acetoxypregn-5-en-20-one caused by amines, is presented. The titled compounds were evaluated for their potency to regulate sterol and triglyceride biosynthesis in human hepatoma Hep G2 cells in comparison with 25-hydroxycholesterol. Three [17(20)E]-pregna-5,17(20)-dien-21-oyl amides at a concentrations of 5 μM inhibited sterol biosynthesis and stimulated triglyceride biosynthesis; their regulatory potency was dependent on the structure of amide moiety; the isomeric [17(20)Z]-pregna-5,17(20)-dien-21-oyl amides were inactive.

• Authors: Sergey V Stulov, Olga V Mankevich, Nikita O Dugin, Roman A Novikov, Vladimir P Timofeev, Alexander Yu Misharin
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 23 Issue 7 Pg. 2014-8 (Apr 01 2013) ISSN: 1464-3405 [Electronic] England
• PMID: 23466231 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2013 Elsevier Ltd. All rights reserved.

Chemical References

• Amides
• Pregnadienes
• Sterols
• Triglycerides

Topics

• Amides (chemical synthesis, chemistry, pharmacology)
• Dose-Response Relationship, Drug
• Hep G2 Cells
• Humans
• Molecular Conformation
• Pregnadienes (chemical synthesis, chemistry, pharmacology)
• Sterols (antagonists & inhibitors, biosynthesis)
• Triglycerides (antagonists & inhibitors, biosynthesis)