title: 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: Orekhovich Institute of Biomedical Chemistry, RAMS, Moscow, Russia.
authors: Sergey V
authors: SV
authors: Stulov
authors: Olga V
authors: OV
authors: Mankevich
authors: Nikita O
authors: NO
authors: Dugin
authors: Roman A
authors: RA
authors: Novikov
authors: Vladimir P
authors: VP
authors: Timofeev
authors: Alexander Yu
authors: AY
authors: Misharin
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D056945:Hep G2 Cells; D006801:Humans; D008968:Molecular Conformation; D011245:Pregnadienes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013261:Sterols / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D014280:Triglycerides / Q000037:antagonists & inhibitors* / Q000096:biosynthesis
chemical_list: D000577:Amides; D011245:Pregnadienes; D013261:Sterols; D014280:Triglycerides