11,11’-dideoxyverticillin A, 11,11’-dideoxyverticillin, CHEMBL2172426
|Molar mass||664.84 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Dideoxyverticillin A (+)-11,11’-dideoxyverticillin A is a complex epipolythiodioxopiperazine  initially isolated from the marine fungus Penicillium sp. in 1999  has also been found in the marine fungus (Bionectriaceae), and belongs to a class of naturally occurring 2,5-diketopiperazines. Dideoxyverticillin A potently inhibits the tyrosine kinase activity of the epidermal growth factor receptor (median inhibitory concentration = 0.14 nM), exhibits antiangiogenic activity, and has efficacy against several cancer cell lines. Its reported anticancer mechanism is that it acts as a farnesyl transferase inhibitor. Dozens of semi-synthetic anticancer compounds have been made from Dideoxyverticillin A. Dimeric derivatives are reported to have better anticancer activity. The enantioselective first total synthesis of (+)-11,11’-dideoxyverticillin A, the structure of which contains many sterically congested, contiguous stereogenic centers as well as acid- and base-labile and redox-sensitive functionality, was biosynthetically inspired and achieved with high levels of chemical sophistication.
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