77495-85-3Relevant academic research and scientific papers
A convenient method for the preparation of 20-[18O]-labeled ingenol
Pospí?il, Ji?í,Béres, Tibor,Strnad, Miroslav
, p. 1421 - 1424 (2017/03/16)
A short and efficient protecting group-free synthesis of isotopically labeled 20-[18O]-ingenol has been developed. Based on a highly selective (only one out of four hydroxy groups) Mitsunobu reaction of ingenol with 18O2-acetic acid and subsequent methanolysis, this route yielded the desired 20-[18O]-ingenol in high yield and chemical and isotopic purity.
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.
