Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
2027551 | Steroids | 2015 | 8 Pages |
•For the first time two approaches to stereoselective synthesis of steroid containing 5Z,9Z-dienoic acids have been developed.•High inhibitory activity of the synthesized acids against human topoisomerase I was found.•The structures of all novel compounds were confirmed by NMR measurements.
Two approaches to stereoselective synthesis of steroid 5Z,9Z-dienoic acids were developed, the first one being based on the cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and 1,2-diene cholesterol derivatives on treatment with EtMgBr catalyzed by Cp2TiCl2, while the other involving the synthesis of esters of hydroxy steroids with (5Z,9Z)-tetradeca-5,9-dienedioic acid, prepared in two steps using homo-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran as the key step. High inhibitory activity of the synthesized acids against human topoisomerase I (hTop1) was found.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide