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

Sergey V Stulov, Olga V Mankevich, Nikita O Dugin, Roman A Novikov, Vladimir P Timofeev, Alexander Yu Misharin

Orekhovich Institute of Biomedical Chemistry, RAMS, Moscow, Russia.

Bioorganic & medicinal chemistry letters 2013 Apr 1

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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. Copyright © 2013 Elsevier Ltd. All rights reserved.

Citation

Sergey V Stulov, Olga V Mankevich, Nikita O Dugin, Roman A Novikov, Vladimir P Timofeev, Alexander Yu Misharin. Pregna-5,17(20)-dien-21-oyl amides affecting sterol and triglyceride biosynthesis in Hep G2 cells. Bioorganic & medicinal chemistry letters. 2013 Apr 1;23(7):2014-8