Synthesis of novel 24-amino-25,26,27-trinorlanost-8-enes: cytotoxic and apoptotic potential in U937 cells
- Bioorg Med Chem. 2015 May 1;23(9):2270-80. doi: 10.1016/j.bmc.2015.02.034.
Affiliations
- 1. Department of Chemistry, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Ireland.
- 2. School of Food and Nutritional Sciences, University College Cork, Ireland.
- 3. School of Agriculture and Food Science, University College Dublin, Dublin 4, Ireland.
- 4. Food Biosciences Department, Teagasc Food Research Centre, Ashtown, Dublin 15, Ireland.
- 5. Department of Zoology, Ecology and Plant Science, University College Cork, Ireland.
- 6. School of Food and Nutritional Sciences, University College Cork, Ireland. Electronic address: [email protected].
- 7. Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Ireland. Electronic address: [email protected].
- 8. Department of Chemistry, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Ireland. Electronic address: [email protected].
PMID: 25800433
DOI: 10.1016/j.bmc.2015.02.034
Abstract
In the present study, the synthesis of a range of novel 24-amino-25,26,27-trinorlanost-8-ene derivatives including 24-piperadino-trinorlanost-8-enes, 24-piperazino-trinorlanost-8-enes, 24-morpholino-trinorlanost-8-enes, and 24-diethylamino-trinorlanost-8-enes is reported and their cytotoxic and apoptotic potential evaluated in U937 cell lines. Excellent IC₅₀ results for piperidine and 1-(2-hydroxyethyl)piperazine derivatives have been observed (IC₅₀ values of 1.9 μM and 2.7 μM in U937 cells, respectively).
Keywords
Apoptosis; Lanostanes; Oxidative cleavage; Reductive amination; U937 cells.