13,14-dihydro-16,16-difluoro Prostaglandin J2

Prostaglandin J₂ (PGJ₂) is an analog of PGD₂ that can inhibit both platelet aggregation and cell growth.^1,2,3 However, it is not clear whether these effects are initiated by PGJ₂ or a derivative. 13,14-dihydro-16,16-difluoro PGJ₂ is an analog of PGJ₂. While its biological activities have not been evaluated, it should be noted that the addition of two electron-withdrawing fluorine atoms has been used to stabilize prostanoids and significantly delay degradation in vivo.⁴ Importantly, 13,14-dihydro PGE₁ has activity that is comparable to that of PGE₁, suggesting that this analog of PGJ₂ could be biologically active.^5,6

1.Bundy, G.L., Morton, D.R., Peterson, D.C., et al.Synthesis and platelet aggregation inhibiting activity of prostaglandin D analoguesJ. Med. Chem.26(6)790-799(1983) 2.Mahmud, I., Smith, D.L., Whyte, M.A., et al.On the identification and biological properties of prostaglandin J2Prostaglandins Leukot. Med.16(2)131-146(1984) 3.Fukushima, M.Prostaglandin J2 - anti-tumor and anti-viral activities and the mechanisms involvedEicosanoids3(4)189-199(1990) 4.Hatano, Y., Kohli, J.D., Goldberg, L.I., et al.Vascular relaxing activity and stability studies of 10,10-difluoro-13,14-dehydroprostacyclinProceedings of the National Academy of Sciences of the United States of America77(11)6846-6850(1980) 5.ÄnggÅrd, E.The biological activities of three metabolites of prostaglandin E1Acta Physiologica Scandinavica66509-510(1966) 6.Hamberg, M., and Samuelsson, B.On the metabolism of prostaglandins E1 and E2 in manJ. Biol. Chem.246(22)6713-6721(1971)