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Novel side chain modified Δ8(14)-15-ketosterols
| Content Provider | Semantic Scholar |
|---|---|
| Author | Misharin, Alexander Yu. Ivanov, Vitali S. Mehtiev, Arif R. Morozevich, Galina E. Timofeev, Vladimir P. |
| Copyright Year | 2007 |
| Abstract | Abstract Synthesis of five novel Δ8(14)-15-ketosterols comprising modified side chains starting from ergosterol is described. Ergosteryl acetate was converted into (22 E )-3β-acetoxy-5α-ergosta-8(14),22-dien-15-one through three stages in 32% overall yield; further transformations of the product obtained led to (22 E )-3β-hydroxy-5α-ergosta-8(14),22-dien-15-one, (22 S ,23 S )-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one, (22 R ,23 R )-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one, (22 R ,23 R )-5α-ergost-8(14)-en-15-on-3β,22,23-triol and (22 R ,23 R )-3β-hydroxy-22,23-isopropylidenedioxy-5α-ergost-8(14)-en-15-one. New Δ8(14)-15-ketosterols were evaluated for their cytotoxicity and effects on sterol biosynthesis in human hepatoma Hep G2 cells in comparison with known 3β-hydroxy-5α-cholest-8(14)-en-15-one. Among the compounds tested, (22 R ,23 R )-3β-hydroxy-22,23-oxido-5α-ergost-8(14)-en-15-one was found to be the most potent inhibitor of sterol biosynthesis (IC 50 = 0.6 ± 0.2 μM), whereas (22 R ,23 R )-5α-ergost-8(14)-en-15-on-3β,22,23-triol exhibited the highest cytotoxicity (TC 50 = 12 ± 3 μM at a 24 h incubation). |
| Starting Page | 305 |
| Ending Page | 312 |
| Page Count | 8 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/j.steroids.2006.12.002 |
| Volume Number | 72 |
| Alternate Webpage(s) | https://api.elsevier.com/content/article/pii/S0039128X06002637 |
| Alternate Webpage(s) | https://www.sciencedirect.com/science/article/pii/S0039128X06002637?dgcid=api_sd_search-api-endpoint |
| Journal | Steroids |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
