To improve rupestonic acid biological activities, ten rupestonic acid benzyl ester derivatives were synthesized in the presence of DCC/DMAP with the rupestonic acid and substituted benzyl alcohol as starting materials. The synthesized compounds 2a similar to 2j were confirmed by the methods of IR, (1)H NMR, ESI-MS and preliminarily assayed in vitro against influenza viruses A3, B and herpes simplex virus I (HSV-I), herpes simplex virus II (HSV-II). The results showed that most of the synthesized compounds had distinct inhibition against influenza viruses, 2e exhibited in vitro inhibitory activity against both influenza A3 and B viruses with IC(50) values of 5.5, 5.5 mu mol/L, respectively, and 2i showed higher activity against influenza A virus with an IC(50) value of 7.8 mu mol/L. Therefore, compounds 2e, 2i can be as lead compounds for anti-flu agent. Most of the compounds showed higher inhibition against HSV-I and HSV-II viruses at 0.1 mu g/mL concentration.
Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Nat Prod Chem, Urumqi 830011, Peoples R China;Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
Yong Jianping,Aisa Haji Akber,Nie Lifei. synthesis of rupestonic acid benzyl ester derivatives and in vitro anti influenza virus and herpes simplex type i and ii viruses[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2009,29(10):1640-1644.