861446-17-5Relevant articles and documents
Synthesis of 4′-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines
Wong, Yong,Osmond, Gregory,Brewer, Kenneth I.,Tyler, Douglas S.,Andrus, Merritt B.
supporting information; experimental part, p. 1198 - 1201 (2010/06/15)
4′-Ester analogs of the disease preventative agent resveratrol were synthesized and evaluated for their potential as anti-melanoma and pancreatic cancer agents. A decarbonylative Heck coupling was used to assemble the protected stilbene core structure. Th
Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings
Andrus, Merritt B.,Liu, Jing
, p. 5811 - 5814 (2007/10/03)
Protected 3,5-hydroxy-benzoyl chlorides 3 were coupled with styrenes 4 to give hydroxylated stilbenes, analogs of resveratrol, an important antioxidant disease preventative agent isolated from grape skins and other dietary sources. Levulinate and chloroacetate protecting groups allowed for the selective production of mono- and di-acetate variations under palladium-N-heterocyclic carbene (NHC) catalyzed decarbonylative coupling conditions. Fluorinated analogs were also produced using Heck conditions with bromofluorobenzenes. Human HL-60 cell assays showed the 4′-acetoxy variant 11 to have improved activity (ED50 17 μM) relative to resveratrol (24 μM).