Synthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a] pyridine-fused steroids

Lopes, Susana M. M.; Sousa, Emanuel P.; Barreira, Luísa; F. Marques, C.; Rodrigues, Maria João; Pinho e Melo, Teresa M. V. D.

http://hdl.handle.net/10400.1/13108

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Authors

Rodrigues, Maria João

Pinho e Melo, Teresa M. V. D.

Abstract(s)

Regio-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.