Lopes, Susana M. M.Sousa, Emanuel P.Barreira, LuísaF. Marques, C.Rodrigues, Maria JoãoPinho e Melo, Teresa M. V. D.2019-11-202019-11-202017-060039-128X1878-5867http://hdl.handle.net/10400.1/13108Regio-and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo [1,5-a]pyridine fused steroids via [8 pi + 2 pi] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity. Thus, results indicate that the presence of the benzyl group is important to ensure cytotoxicity.engC-17 pyrazolinyl derivativesDiazafulvenium methidesProstate-cancerProliferationSynthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a] pyridine-fused steroidsjournal article10.1016/j.steroids.2017.03.006