期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 27, 页码 5187-5194出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200619
关键词
Total synthesis; Natural products; Steroids; Structure-activity relationships
资金
- MAREX-Exploring Marine Resources for Bioactive Compounds: From Discovery to Sustainable Production and Industrial Applications [245137]
- Ministero dell'Universita e della Ricerca (MIUR)
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.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据