59086-90-7Relevant academic research and scientific papers
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.
On the Chemistry of Ingenol, II. Esters of Ingenol and δ7,8-Isoingenol
Sorg, Bernd,Hecker, Erich
, p. 748 - 756 (2007/10/02)
Preparation and purification of 3-acylated of ingenol (1a) structurally related to naturally occuring, irritant and cocarcinogenic principles are described.It is shown that 3-acylated partly rearrange to corresponding 5-acylates when they are chromatograp
