ipomoeassin-f and tiglic-acid

An efficient synthetic route for ipomoeassin F and its tiglate-modified analogues was developed. The route features late-stage conformation-controlled highly regioselective esterification of the glucose diol in the disaccharide core. The results from the NCI-60 cell line screens of ipomoeassin F were reported for the first time. Moreover, two new C-3-cinnamoyl-Glcp analogues (2 and 3) were prepared. Their in-house cytotoxicity data convey an important message that both identity and positioning of the two α,β-unsaturated esters are crucial. They are not interchangeable.

Topics: Cell Line, Tumor; Cinnamates; Crotonates; Drug Screening Assays, Antitumor; Drug Synergism; Glycoconjugates; Hemiterpenes; Humans; Spectrum Analysis