59086-90-7Relevant articles and documents
Synthesis of modified ingenol esters
Appendino, Giovanni,Tron, Gian Cesare,Cravotto, Giancarlo,Palmisano, Giovanni,Annunziata, Rita,Baj, Germano,Surico, Nicola
, p. 3413 - 3420 (2007/10/03)
Synthetic protocols for the manipulation of the polyhydroxylated southern region of ingenol (1a) were developed, and a series of isosteres of the anticancer compound ingenol 3,20-dibenzoate (1b) was prepared. The biological evaluation of these compounds showed that cytotoxicity was relatively tolerant to changes at C-20, while PKC activation was markedly affected by these modifications. These data suggest that chemical manipulation can effectively dissect cytotoxicity and tumour-promoting activity (or potential) of ingenoids, affording more optimal candidates for development, like 20-deoxy-20-fluoroingenol 3,20-dibenzoate (5b). In mild acidic medium, an unexpected vinylogous retro-pinacol rearrangement of ingenol to a tigliane derivative was observed.