Abstract
In this thesis, I develop a synthetic route for the preparation of salvianolic acid C, rosmarinic acid, and lithospermic acid derivatives. I also explore the RNA cleaving ability and antiviral activities of benzo[c]cinnoline N-oxide, which can cleave DNA upon UV irradiation. Furthermore, I report a photo-induced DNA cleaving processes by using ruthenium and osmium oximates under aerobic conditions. In Part 1 of this thesis, derivatives of phenolic acids extracted from Salvia miltiorrhiza were synthesized. These phenolic acids including heptamethyl lithospermic acid derivative, hexamethyl salvianolic acid C, and pentamethyl rosmarinic acid. The key step involved a Heck-type coupling followed by cyclization. In Part 2, I found one of the azoxy compound, benzo[c]cinnoline N-oxide, can cleave RNA upon exposure to UV light. Under irradiation with UV light at 365 nm for 30 minutes, benzo[c]cinnoline N-oxide was able to inactivate herpes simplex virus type I in three strains. Through polymerase chain reaction, the DNA of azoxy treated virus were cleaved. Moreover, I demonstrated that benzo[c]cinnoline N-oxide cleaved DNA dominantly at the guanine residue by photolysis with UV light at 365 nm. In Part 3, I reported that single-strand DNA cleavage can be accomplished by photolysis of di- and triruthenium complexes and triosmium oximates with exposure to 350-nm UV light under aerobic conditions. This photo-induced cleaving process was pH-dependent over pH 5.0–8.0 and exhibited the greatest cleaving ability at acidic condition at pH 5.0.