Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 27, Pages 5187-5194Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200619
Keywords
Total synthesis; Natural products; Steroids; Structure-activity relationships
Categories
Funding
- MAREX-Exploring Marine Resources for Bioactive Compounds: From Discovery to Sustainable Production and Industrial Applications [245137]
- Ministero dell'Universita e della Ricerca (MIUR)
Ask authors/readers for more resources
A concise route to the pregnane X receptor (PXR) agonist solomonsterol B, a natural product isolated from the marine sponge Theonella swinhoei, has been developed starting from commercially available hyodeoxycholic acid. The synthesis features a one-carbon side chain degradation and the refunctionalization of the A and B rings to install the desired trans junction and the two hydroxy groups at C2 and C3 in a trans relationship. The protocol proceeded with good yields (10?% over 13 steps), also allowing the preparation of a side chain-modified derivative useful for a preliminary structureactivity relationship on PXR. The pharmacological characterization of solomonsterol B demonstrated that this compound was a PXR agonist in a transactivation assay, and when it was incubated with liver cells, it increased the expression of PXR-regulated genes. These data support the development of sponge steroids as PXR ligands endowed with therapeutic potential.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available