| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1394598 | European Journal of Medicinal Chemistry | 2011 | 10 Pages |
A series of steroid and azasteroid analogues containing a six-membered ring A with various functionalities were synthesized. Furthermore, the syntheses of tetracyclic analogues bearing a five-membered A-ring and the syntheses of a number of bicyclic secosteroid analogues were carried out. All compounds were tested for their antibacterial, antifungal and cytotoxic activities. Among all tested compounds 7 and 9 showed outstanding cytotoxic activities but were devoid of antimicrobial activities. The cytotoxic activities of compounds 7, 9 and 10 were initially verified by the National Cancer Institute (NCI) in a one-dose 60 cell assay. In accordance with our results 7 and 9 satisfied pre-determined threshold inhibition criteria for progression to the 5-dose NCI screening, which revealed a selective activity profile for both candidates.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights►Steroid analogues with different ring A sizes and functionalities were synthesized. ►Antibacterial, antifungal and cytotoxic activities were tested of all compounds. ►A rigid steroid backbone was found to be indispensable for cytotoxic activities. ►A Michael acceptor system implemented in ring A reinforced cytotoxic activities. ►Selected compounds satisfied NCI pre-determined threshold inhibition criteria.
