Abstract
In this thesis, I report the application of “counterattack reagent” hexamethyldisilathiane on the accomplish of a series of novel double functional group transformations. Furthermore, I synthesize the derivatives of nordihydroguaiaretic acid (NDGA) and novel platinum complexes as a new anticancer agents. In Part 1 of this thesis, a series of novel double functional group transformations were established. These transformations convert nitrocycloalkenes to □-substituted ketoximes in “one flask” procedure. Sophisticated mechanisms are involved in these reactions. In those efficient tandem processes, hexamethyldisilathiane acts as a counterattack reagent. In Part 2 of this thesis, water soluble derivatives of nordihydroguaiaretic acid (NDGA), Malotse-M3N, was synthesized by coupling tri-O-methyl-NDGA (M3N) with maltose in the presence of boron trifluoride-diethyl etherate in CH2Cl2 and deprotection by use of sodium methoxide. Maltose-M3N inhibits the growth of the five human cancer cell lines in vitro with IC50 values of 20 □M to 40 □M. Nevertheless, inhibition of CDC2 and survivin expression is observed. Four daily intratumoral injections of Malotse-M3N into C3 tumors also effectively suppresses CDC2 and survivin expression and induces apoptosis throughout the whole tumor tissues without toxicities. In Part 3 of this thesis, A series of novel organoplatinum complexes were synthesized by adding sodium 2-mercaptopyridine N-oxide and a series of sulfoxides to K2PtCl4 in DMF and H2O (1 : 5) condition. In vitro growth inhibitory effect of those organoplatinum complexes were evaluated in human cancer cell lines Cal27. We found five of those organoplatinum complexes exhibited noteworthy anticancer activity.